Skip to main content
SpringerLink
Log in

Arylation with Diaryliodonium Salts

  • Chapter
  • First Online:
Hypervalent Iodine Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 373))

Abstract

This chapter focuses on recent developments in metal-free and metal-catalyzed arylations with diaryliodonium salts (diaryl-λ3-iodanes). Synthetic routes to diaryliodonium salts are briefly described, and chemoselectivity trends with unsymmetric iodonium salts are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Zhdankin VV (2013) Hypervalent iodine chemistry. Wiley, Chichester

    Book  Google Scholar 

  2. Wirth T (2003) Topic in current chemistry. Springer, Berlin

    Google Scholar 

  3. Zhdankin VV, Stang PJ (2008) Chem Rev 108:5299

    Article  CAS  Google Scholar 

  4. Merritt EA, Olofsson B (2009) Angew Chem Int Ed 48:9052

    Article  CAS  Google Scholar 

  5. Yamaoka N (2012) Synlett 23:478

    Article  Google Scholar 

  6. Grushin VV (2000) Chem Soc Rev 29:315

    Article  CAS  Google Scholar 

  7. Yusubov MS, Maskaev AV, Zhdankin VV (2011) Arkivoc (i):370

    Google Scholar 

  8. Crivello JV (1999) J Polym Sci A Polym Chem 37:4241

    Article  CAS  Google Scholar 

  9. Lalevée J, Mokbel H, Fouassier J-P (2015) Molecules 20:7201

    Article  CAS  Google Scholar 

  10. Lalevée J, Blanchard N, Tehfe M-A, Morlet-Savary F, Fouassier JP (2010) Macromolecules 43:10191

    Article  CAS  Google Scholar 

  11. Zhang Y, Han J, Liu Z-J (2015) RSC Adv 5:25485

    Article  CAS  Google Scholar 

  12. Lu M-Z, Loh T-P (2014) Org Lett 16:4698

    Article  CAS  Google Scholar 

  13. Buslov I, Hu X (2014) Adv Synth Catal 356:3325

    Article  CAS  Google Scholar 

  14. Stang PJ, Zhdankin VV (1993) J Am Chem Soc 115:9808

    Article  CAS  Google Scholar 

  15. Olenyuk B, Whiteford JA, Stang PJ (1996) J Am Chem Soc 118:8221

    Article  CAS  Google Scholar 

  16. Stang PJ, Zhdankin VV (1996) Chem Rev 96:1123

    Article  CAS  Google Scholar 

  17. van de Veerdonk FL, Smeekens SP, Joosten LAB, Kullberg BJ, Dinarello CA, van der Meer JWM, Netea MG (2010) Proc Natl Acad Sci U S A 107:3030

    Article  Google Scholar 

  18. Postnikov PS, Guselnikova OA, Yusubov MS, Yoshimura A, Nemykin VN, Zhdankin VV (2015) J Org Chem 80:5783

    Article  CAS  Google Scholar 

  19. Alcock NW, Countryman RM (1977) J Chem Soc Dalton Trans 217

    Google Scholar 

  20. Ochiai M (2003) Hypervalent iodine chemistry. In: Wirth T (ed) Topics in current chemistry, vol 224. Springer, Berlin, p 5

    Google Scholar 

  21. Ledwith A, Al-Kass S, Sherrington DC, Bonner P (1981) Polymer 22:143

    Article  CAS  Google Scholar 

  22. Miyamoto K, Hirobe M, Saito M, Shiro M, Ochiai M (2007) Org Lett 9:1995

    Article  CAS  Google Scholar 

  23. Okuyama T, Takino T, Sueda T, Ochiai M (1995) J Am Chem Soc 117:3360

    Article  CAS  Google Scholar 

  24. Oae S, Uchida Y (1991) Acc Chem Res 24:202

    Article  CAS  Google Scholar 

  25. Ochiai M, Kitagawa Y, Toyonari M (2003) Arkivoc (iv):43

    Google Scholar 

  26. Norrby P-O, Petersen TB, Bielawski M, Olofsson B (2010) Chem Eur J 16:8251

    Article  CAS  Google Scholar 

  27. Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B (2013) Chem Eur J 19:10334

    Article  CAS  Google Scholar 

  28. Kita Y, Dohi T (2015) Chem Rec 15. doi:10.1002/tcr.201500020

    Google Scholar 

  29. Dohi T, Ito M, Morimoto K, Minamitsuji Y, Takenaga N, Kita Y (2007) Chem Commun 4152

    Google Scholar 

  30. Dohi T, Yamaoka N, Kita Y (2010) Tetrahedron 66:5775

    Article  CAS  Google Scholar 

  31. Beringer FM, Galton SA, Huang SJ (1962) J Am Chem Soc 84:2819

    Article  CAS  Google Scholar 

  32. Pinto de Magalhães H, Lüthi HP, Togni A (2012) Org Lett 14:3830

    Article  CAS  Google Scholar 

  33. Pinto de Magalhães H, Lüthi HP, Togni A (2014) J Org Chem 79:8374

    Article  CAS  Google Scholar 

  34. Beringer FM, Huang SJ (1964) J Org Chem 29:445

    Article  CAS  Google Scholar 

  35. Kitamura T, Todaka M, Fujiwara Y (2002) Org Synth 78:104

    Article  CAS  Google Scholar 

  36. Cadogan JIG, Rowley AG, Sharp JT, Sledzinski B, Wilson NH (1975) J Chem Soc Perkin Trans 1 1072

    Google Scholar 

  37. Hickman AJ, Sanford MS (2012) Nature 484:177

    Article  CAS  Google Scholar 

  38. Canty AJ, Rodemann T, Ryan JH (2007) In: Robert West AFH, Mark JF (eds) Advances in organometallic chemistry, vol 55. Academic, New York, p 279

    Google Scholar 

  39. Deprez NR, Sanford MS (2009) J Am Chem Soc 131:11234

    Article  CAS  Google Scholar 

  40. Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330

    Article  CAS  Google Scholar 

  41. Canty AJ, Ariafard A, Sanford MS, Yates BF (2013) Organometallics 32:544

    Article  CAS  Google Scholar 

  42. Kalberer EW, Whitfield SR, Sanford MS (2006) J Mol Catal A Chem 251:108

    Article  CAS  Google Scholar 

  43. Chen B, Hou X-L, Li Y-X, Wu Y-D (2011) J Am Chem Soc 133:7668

    Article  CAS  Google Scholar 

  44. Wang B, Graskemper JW, Qin L, DiMagno SG (2010) Angew Chem Int Ed 49:4079

    Article  CAS  Google Scholar 

  45. Martin-Santamaria S, Carroll MA, Carroll CM, Carter CD, Rzepa HS, Widdowson DA, Pike VW (2000) Chem Commun 649

    Google Scholar 

  46. Yamada Y, Okawara M (1972) Bull Chem Soc Jpn 45:1860

    Article  CAS  Google Scholar 

  47. Wang B, Cerny RL, Uppaluri S, Kempinger JJ, DiMagno SG (2010) J Fluor Chem 131:1113

    Article  CAS  Google Scholar 

  48. Kasahara T, Jang YJ, Racicot L, Panagopoulos D, Liang SH, Ciufolini MA (2014) Angew Chem Int Ed 53:9637

    Article  CAS  Google Scholar 

  49. Chen D-W, Ochiai M (1999) J Org Chem 64:6804

    Article  CAS  Google Scholar 

  50. Chen D-W, Takai K, Ochiai M (1997) Tetrahedron Lett 38:8211

    Article  CAS  Google Scholar 

  51. Phipps RJ, Grimster NP, Gaunt MJ (2008) J Am Chem Soc 130:8172

    Article  CAS  Google Scholar 

  52. Toh QY, McNally A, Vera S, Erdmann N, Gaunt MJ (2013) J Am Chem Soc 135:3772

    Article  CAS  Google Scholar 

  53. Jalalian N, Petersen TB, Olofsson B (2012) Chem Eur J 18:14140

    Article  CAS  Google Scholar 

  54. Huang X, Zhu Q, Xu Y (2001) Synth Commun 31:2823

    Article  CAS  Google Scholar 

  55. Kumar Muthyala M, Choudhary S, Pandey K, Shelke GM, Jha M, Kumar A (2014) Eur J Org Chem 2014:2365

    Article  CAS  Google Scholar 

  56. Hartmann C, Meyer V (1894) Ber Dtsch Chem Ges 27:502

    Article  Google Scholar 

  57. Beringer FM, Drexler M, Gindler EM, Lumpkin CC (1953) J Am Chem Soc 75:2705

    Article  CAS  Google Scholar 

  58. Bielawski M, Zhu M, Olofsson B (2007) Adv Synth Catal 349:2610

    Article  CAS  Google Scholar 

  59. Bielawski M, Olofsson B (2007) Chem Commun 2521

    Google Scholar 

  60. Zhu M, Jalalian N, Olofsson B (2008) Synlett 592

    Google Scholar 

  61. Bielawski M, Aili D, Olofsson B (2008) J Org Chem 73:4602

    Article  CAS  Google Scholar 

  62. Bielawski M, Olofsson B (2009) Org Synth 86:308

    Article  CAS  Google Scholar 

  63. Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K (2005) J Am Chem Soc 127:12244

    Article  CAS  Google Scholar 

  64. Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y (2005) Angew Chem Int Ed 44:6193

    Article  CAS  Google Scholar 

  65. Creutz SE, Peters JC (2014) J Am Chem Soc 136:1105

    Article  CAS  Google Scholar 

  66. Wu B, Yoshikai N (2015) Angew Chem Int Ed. doi:10.1002/anie.201503134

    Google Scholar 

  67. Matsuzaki K, Okuyama K, Tokunaga E, Shibata N, Saito N, Shiro M (2015) Org Lett 17:3038

    Article  CAS  Google Scholar 

  68. Chun J-H, Pike VW (2012) Eur J Org Chem 4541

    Google Scholar 

  69. Roh KR, Kim JY, Kim YH (1998) Chem Lett 27:1095

    Article  Google Scholar 

  70. Hossain MD, Kitamura T (2007) Bull Chem Soc Jpn 80:2213

    Article  CAS  Google Scholar 

  71. Hossain MD, Ikegami Y, Kitamura T (2006) J Org Chem 71:9903

    Article  CAS  Google Scholar 

  72. Merritt EA, Malmgren J, Klinke FJ, Olofsson B (2009) Synlett 2277

    Google Scholar 

  73. Dohi T, Yamaoka N, Itani I, Kita Y (2011) Aust J Chem 64:529

    Article  CAS  Google Scholar 

  74. Kitamura T, Matsuyuki J, Taniguchi H (1994) Synthesis 14

    Google Scholar 

  75. Ochiai M, Toyonari M, Sueda T, Kitagawa Y (1996) Tetrahedron Lett 37:8421

    Article  CAS  Google Scholar 

  76. Koser GF, Wettach RH, Smith CS (1980) J Org Chem 45:1543

    Article  CAS  Google Scholar 

  77. Pike VW, Butt F, Shah A, Widdowson DA (1999) J Chem Soc Perkin Trans 1 245

    Google Scholar 

  78. Carroll MA, Pike VW, Widdowson DA (2000) Tetrahedron Lett 41:5393

    Article  CAS  Google Scholar 

  79. Margida AJ, Koser GF (1984) J Org Chem 49:3643

    Article  CAS  Google Scholar 

  80. Phipps RJ, Gaunt MJ (2009) Science 323:1593

    Article  CAS  Google Scholar 

  81. Matsuzaki K, Okuyama K, Tokunaga E, Shiro M, Shibata N (2014) ChemOpen 3:233

    CAS  Google Scholar 

  82. Ito M, Itani I, Toyoda Y, Morimoto K, Dohi T, Kita Y (2012) Angew Chem Int Ed 51:12555

    Article  CAS  Google Scholar 

  83. Lubriks D, Sokolovs I, Suna E (2011) Org Lett 13:4324

    Article  CAS  Google Scholar 

  84. Sokolovs I, Lubriks D, Suna E (2014) J Am Chem Soc 136:6920

    Article  CAS  Google Scholar 

  85. Hu B, Miller WH, Neumann KD, Linstad EJ, DiMagno SG (2015) Chem Eur J 21:6394

    Article  CAS  Google Scholar 

  86. Xie F, Zhang Z, Yu X, Tang G, Li X (2015) Angew Chem Int Ed 54:7405

    Article  CAS  Google Scholar 

  87. Beringer FM, Brierley A, Drexler M, Gindler EM, Lumpkin CC (1953) J Am Chem Soc 75:2708

    Article  CAS  Google Scholar 

  88. Lubinkowski JJ, Gomez M, Calderon JL, McEwen WE (1978) J Org Chem 43:2432

    Article  CAS  Google Scholar 

  89. Lubinkowski JJ, Knapczyk JW, Calderon JL, Petit LR, McEwen WE (1975) J Org Chem 40:3010

    Article  CAS  Google Scholar 

  90. Schäfer S, Wirth T (2010) Angew Chem Int Ed 49:2786

    Article  CAS  Google Scholar 

  91. Carroll MA, Wood RA (2007) Tetrahedron 63:11349

    Article  CAS  Google Scholar 

  92. Guo F, Wang L, Wang P, Yu J, Han J (2012) Asian J Org Chem 1:218

    Article  CAS  Google Scholar 

  93. Li J, Liu L (2012) RSC Adv 2:10485

    Article  CAS  Google Scholar 

  94. Landge KP, Jang KS, Lee SY, Chi DY (2012) J Org Chem 77:5705

    Article  CAS  Google Scholar 

  95. Tinnis F, Stridfeldt E, Lundberg H, Adolfsson H, Olofsson B (2015) Org Lett 17:2688

    Article  CAS  Google Scholar 

  96. Li P, Cheng G, Zhang H, Xu X, Gao J, Cui X (2014) J Org Chem 79:8156

    Article  CAS  Google Scholar 

  97. Peng J, Chen C, Wang Y, Lou Z, Li M, Xi C, Chen H (2013) Angew Chem Int Ed 52:7574

    Article  CAS  Google Scholar 

  98. Kang S-K, Lee H-W, Choi W-K, Hong R-K, Kim J-S (1996) Synth Commun 26:4219

    Article  CAS  Google Scholar 

  99. Kang S-K, Lee S-H, Lee D (2000) Synlett 1022

    Google Scholar 

  100. Zhou T, Chen Z-C (2002) Synth Commun 32:903

    Article  CAS  Google Scholar 

  101. Lv T, Wang Z, You J, Lan J, Gao G (2013) J Org Chem 78:5723

    Article  CAS  Google Scholar 

  102. Howell TO, Huckaba AJ, Hollis TK (2014) Org Lett 16:2570

    Article  CAS  Google Scholar 

  103. Pankajakshan S, Chng ZG, Ganguly R, Loh TP (2015) Chem Commun 51:5929

    Article  CAS  Google Scholar 

  104. Zhu D, Liu Q, Luo B, Chen M, Pi R, Huang P, Wen S (2013) Adv Synth Catal 355:2172

    Article  CAS  Google Scholar 

  105. Riedmüller S, Nachtsheim BJ (2013) Beilstein J Org Chem 9:1202

    Article  CAS  Google Scholar 

  106. Liu Z, Zhu D, Luo B, Zhang N, Liu Q, Hu Y, Pi R, Huang P, Wen S (2014) Org Lett 16:5600

    Article  CAS  Google Scholar 

  107. Wang Y, Chen C, Peng J, Li M (2013) Angew Chem Int Ed 52:5323

    Article  CAS  Google Scholar 

  108. Su X, Chen C, Wang Y, Chen J, Lou Z, Li M (2013) Chem Commun 49:6752

    Article  CAS  Google Scholar 

  109. Wang Y, Chen C, Zhang S, Lou Z, Su X, Wen L, Li M (2013) Org Lett 15:4794

    Article  CAS  Google Scholar 

  110. Pang X, Chen C, Su X, Li M, Wen L (2014) Org Lett 16:6228

    Article  CAS  Google Scholar 

  111. Aradi K, Novák Z (2015) Adv Synth Catal 357:371

    Article  CAS  Google Scholar 

  112. Li J, Wang H, Sun J, Yang Y, Liu L (2014) Org Biomol Chem 12:7904

    Article  CAS  Google Scholar 

  113. Vaddula B, Leazer J, Varma RS (2012) Adv Synth Catal 354:986

    Article  CAS  Google Scholar 

  114. Kumar D, Reddy VB (2010) Synthesis 1687

    Google Scholar 

  115. Lubriks D, Sokolovs I, Suna E (2012) J Am Chem Soc 134:15436

    Article  CAS  Google Scholar 

  116. Crowder JR, Glover EE, Grundon MF, Kaempfen HX (1963) J Chem Soc 4578

    Google Scholar 

  117. Nilsson C-A, Norström Å, Hansson M, Andersson K (1977) Chemosphere 6:599

    Article  CAS  Google Scholar 

  118. Marsh G, Hu J, Jakobsson E, Rahm S, Bergman Ȧ (1999) Environ Sci Technol 33:3033

    Article  CAS  Google Scholar 

  119. Jalalian N, Ishikawa EE, Silva LF Jr, Olofsson B (2011) Org Lett 13:1552

    Article  CAS  Google Scholar 

  120. Kakinuma Y, Moriyama K, Togo H (2013) Synthesis 45:183

    CAS  Google Scholar 

  121. Chan L, McNally A, Toh QY, Mendoza A, Gaunt MJ (2015) Chem Sci 6:1277

    Article  CAS  Google Scholar 

  122. Ghosh R, Lindstedt E, Jalalian N, Olofsson B (2014) ChemOpen 3:54

    CAS  Google Scholar 

  123. Lindstedt E, Ghosh R, Olofsson B (2013) Org Lett 15:6070

    Article  CAS  Google Scholar 

  124. Sundalam SK, Stuart DR (2015) J Org Chem 80:6456

    Article  CAS  Google Scholar 

  125. Petersen TB, Khan R, Olofsson B (2011) Org Lett 13:3462

    Article  CAS  Google Scholar 

  126. Ghosh R, Olofsson B (2014) Org Lett 16:1830

    Article  CAS  Google Scholar 

  127. Ghosh R, Stridfeldt E, Olofsson B (2014) Chem Eur J 20:8888

    Article  CAS  Google Scholar 

  128. Gao H, Xu Q-L, Keene C, Kürti L (2014) Chem Eur J 20:8883

    CAS  Google Scholar 

  129. Miyagi K, Moriyama K, Togo H (2014) Heterocycles 89:2122

    Article  CAS  Google Scholar 

  130. Castro LCM, Chatani N (2014) Synthesis 46:2312

    Article  CAS  Google Scholar 

  131. Xiong B, Feng X, Zhu L, Chen T, Zhou Y, Au C-T, Yin S-F (2015) ACS Catal 537

    Google Scholar 

  132. Liu F, Yang H, Hu X, Jiang G (2014) Org Lett 16:6408

    Article  CAS  Google Scholar 

  133. Fananas-Mastral M, Feringa BL (2014) J Am Chem Soc 136:9894

    Article  CAS  Google Scholar 

  134. Lin DW, Masuda T, Biskup MB, Nelson JD, Baran PS (2011) J Org Chem 76:1013

    Article  CAS  Google Scholar 

  135. Bhattarai B, Tay J-H, Nagorny P (2015) Chem Commun 51:5398

    Article  CAS  Google Scholar 

  136. Kuriyama M, Hamaguchi N, Onomura O (2012) Chem Eur J 18:1591

    Article  CAS  Google Scholar 

  137. Xu Z-F, Cai C-X, Jiang M, Liu J-T (2014) Org Lett 16:3436

    Article  CAS  Google Scholar 

  138. Cai L, Lu S, Pike VW (2008) Eur J Org Chem 2853

    Google Scholar 

  139. Yusubov MS, Svitich DY, Larkina MS, Zhdankin VV (2013) Arkivoc (i):364

    Google Scholar 

  140. Edwards R, Wirth T, Labelled J (2015) J Label Compd Radiopharm 58:183

    Article  CAS  Google Scholar 

  141. Brooks AF, Topczewski JJ, Ichiishi N, Sanford MS, Scott PJH (2014) Chem Sci 5:4545

    Article  CAS  Google Scholar 

  142. Jacobson O, Kiesewetter DO, Chen X (2015) Bioconjug Chem 26:1

    Article  CAS  Google Scholar 

  143. Cardinale J, Ermert J, Humpert S, Coenen HH (2014) RSC Adv 4:17293

    Article  CAS  Google Scholar 

  144. Rotstein BH, Stephenson NA, Vasdev N, Liang SH (2014) Nat Commun 5:4365

    Article  CAS  Google Scholar 

  145. Der Puy MV (1982) J Fluor Chem 21:385

    Article  Google Scholar 

  146. Pike VW, Aigbirhio FI (1995) J Chem Soc Chem Commun 2215

    Google Scholar 

  147. Chun J-H, Lu S, Lee Y-S, Pike VW (2010) J Org Chem 75:3332

    Article  CAS  Google Scholar 

  148. Xu R, Zanotti-Fregonara P, Zoghbi SS, Gladding RL, Woock AE, Innis RB, Pike VW (2013) J Med Chem 56:9146

    Article  CAS  Google Scholar 

  149. Ross TL, Ermert J, Hocke C, Coenen HH (2007) J Am Chem Soc 129:8018

    Article  CAS  Google Scholar 

  150. Wang B, Qin L, Neumann KD, Uppaluri S, Cerny RL, DiMagno SG (2010) Org Lett 12:3352

    Article  CAS  Google Scholar 

  151. Carroll MA, Nairne J, Smith G, Widdowson DA (2007) J Fluor Chem 128:127

    Article  CAS  Google Scholar 

  152. Ichiishi N, Canty AJ, Yates BF, Sanford MS (2013) Org Lett 15:5134

    Article  CAS  Google Scholar 

  153. Ichiishi N, Brooks AF, Topczewski JJ, Rodnick ME, Sanford MS, Scott PJH (2014) Org Lett 16:3224

    Article  CAS  Google Scholar 

  154. Richarz R, Krapf P, Zarrad F, Urusova EA, Neumaier B, Zlatopolskiy BD (2014) Org Biomol Chem 12:8094

    Article  CAS  Google Scholar 

  155. Zlatopolskiy BD, Zischler J, Krapf P, Zarrad F, Urusova EA, Kordys E, Endepols H, Neumaier B (2015) Chem Eur J 21:5972

    Article  CAS  Google Scholar 

  156. Moon BS, Kil HS, Park JH, Kim JS, Park J, Chi DY, Lee BC, Kim SE (2011) Org Biomol Chem 9:8346

    Article  CAS  Google Scholar 

  157. Saccomanni G, Pascali G, Del Carlo S, Panetta D, De Simone M, Bertini S, Burchielli S, Digiacomo M, Macchia M, Manera C, Salvadori PA (2015) Bioorg Med Chem Lett 25:2532

    Article  CAS  Google Scholar 

  158. Liu Z-D, Chen Z-C (1993) Synthesis 373

    Google Scholar 

  159. Xu J, Zhang P, Gao Y, Chen Y, Tang G, Zhao Y (2013) J Org Chem 78:8176

    Article  CAS  Google Scholar 

  160. Sandin RB, Christiansen RG, Brown RK, Kirkwood S (1947) J Am Chem Soc 69:1550

    Article  CAS  Google Scholar 

  161. Krief A, Dumont W, Robert M (2006) Synlett 484

    Google Scholar 

  162. Wagner AM, Sanford MS (2014) J Org Chem 79:2263

    Article  CAS  Google Scholar 

  163. Racicot L, Kasahara T, Ciufolini MA (2014) Org Lett 16:6382

    Article  CAS  Google Scholar 

  164. Umierski N, Manolikakes G (2013) Org Lett 15:188

    Article  CAS  Google Scholar 

  165. Umierski N, Manolikakes G (2013) Org Lett 15:4972

    Article  CAS  Google Scholar 

  166. Margraf N, Manolikakes G (2015) J Org Chem 80:2582

    Article  CAS  Google Scholar 

  167. Deeming AS, Russell CJ, Hennessy AJ, Willis MC (2014) Org Lett 16:150

    Article  CAS  Google Scholar 

  168. Cullen SC, Shekhar S, Nere NK (2013) J Org Chem 78:12194

    Article  CAS  Google Scholar 

  169. Guo W, Li S, Tang L, Li M, Wen L, Chen C (2015) Org Lett 17:1232

    Article  CAS  Google Scholar 

  170. Yamada Y, Kashima K, Okawara M (1974) Bull Chem Soc Jpn 47:3179

    Article  CAS  Google Scholar 

  171. Lancer KM, Wiegand GH (1976) J Org Chem 41:3360

    Article  CAS  Google Scholar 

  172. Umierski N, Manolikakes G (2012) Org Lett 15:188

    Article  CAS  Google Scholar 

  173. Sun C-L, Shi Z-J (2014) Chem Rev 114:9219

    Article  CAS  Google Scholar 

  174. Neufeldt SR, Sanford MS (2012) Acc Chem Res 45:936

    Article  CAS  Google Scholar 

  175. Bellina F, Rossi R (2009) Tetrahedron 65:10269

    Article  CAS  Google Scholar 

  176. Deprez NR, Sanford MS (2007) Inorg Chem 46:1924

    Article  CAS  Google Scholar 

  177. Rossi R, Bellina F, Lessi M, Manzini C (2014) Adv Synth Catal 356:17

    Article  CAS  Google Scholar 

  178. Rousseaux S, Vrancken E, Campagne J-M (2012) Angew Chem Int Ed 51:10934

    Article  CAS  Google Scholar 

  179. Bonin H, Fouquet E, Felpin F-X (2011) Adv Synth Catal 353:3063

    Article  CAS  Google Scholar 

  180. Hartrampf F, Toombs-Ruane H (2015) Aust J Chem 68:699

    Article  CAS  Google Scholar 

  181. Beringer FM, Daniel WJ, Galton SA, Rubin G (1966) J Org Chem 31:4315

    Article  CAS  Google Scholar 

  182. Chen K, Koser GF (1991) J Org Chem 56:5764

    Article  CAS  Google Scholar 

  183. Oh CH, Kim JS, Jung HH (1999) J Org Chem 64:1338

    Article  CAS  Google Scholar 

  184. Monastyrskyi A, Namelikonda NK, Manetsch R (2015) J Org Chem 80:2513

    Article  CAS  Google Scholar 

  185. Mao S, Geng X, Yang Y, Qian X, Wu S, Han J, Wang L (2015) RSC Adv 5:36390

    Article  CAS  Google Scholar 

  186. Savechenkov PY, Zhang X, Chiara DC, Stewart DS, Ge R, Zhou X, Raines DE, Cohen JB, Forman SA, Miller KW, Bruzik KS (2012) J Med Chem 55:6554

    Article  CAS  Google Scholar 

  187. Chai Z, Wang B, Chen J-N, Yang G (2014) Adv Synth Catal 356:2714

    Article  CAS  Google Scholar 

  188. Brown M, Delorme M, Malmedy F, Malmgren J, Olofsson B, Wirth T (2015) Synlett 26:1573

    Article  CAS  Google Scholar 

  189. Jalalian N, Olofsson B (2010) Tetrahedron 66:5793

    Article  CAS  Google Scholar 

  190. Ochiai M, Kitagawa Y, Takayama N, Takaoka Y, Shiro M (1999) J Am Chem Soc 121:9233

    Article  CAS  Google Scholar 

  191. Aggarwal VK, Olofsson B (2005) Angew Chem 117:5652

    Article  Google Scholar 

  192. Allen AE, MacMillan DWC (2011) J Am Chem Soc 133:4260

    Article  CAS  Google Scholar 

  193. Zhu S, MacMillan DWC (2012) J Am Chem Soc 134:10815

    Article  CAS  Google Scholar 

  194. Bigot A, Williamson AE, Gaunt MJ (2011) J Am Chem Soc 133:13778

    Article  CAS  Google Scholar 

  195. Guo J, Dong S, Zhang Y, Kuang Y, Liu X, Lin L, Feng X (2013) Angew Chem Int Ed 52:10245

    Article  CAS  Google Scholar 

  196. Yan J, Hu W, Rao G (2006) Synthesis 943

    Google Scholar 

  197. Kita Y, Morimoto K, Ito M, Ogawa C, Goto A, Dohi T (2009) J Am Chem Soc 131:1668

    Article  CAS  Google Scholar 

  198. Morimoto K, Yamaoka N, Ogawa C, Nakae T, Fujioka H, Dohi T, Kita Y (2010) Org Lett 12:3804

    Article  CAS  Google Scholar 

  199. Morimoto K, Nakae T, Yamaoka N, Dohi T, Kita Y (2011) Eur J Org Chem 6326

    Google Scholar 

  200. Dohi T, Yamaoka N, Nakamura S, Sumida K, Morimoto K, Kita Y (2013) Chem Eur J 19:2067

    Article  CAS  Google Scholar 

  201. Ackermann L, Dell’Acqua M, Fenner S, Vicente R, Sandmann R (2011) Org Lett 13:2358

    Article  CAS  Google Scholar 

  202. Zhu Y, Bauer M, Ploog J, Ackermann L (2014) Chem Eur J 20:13099

    Article  CAS  Google Scholar 

  203. Eastman K, Baran PS (2009) Tetrahedron 65:3149

    Article  CAS  Google Scholar 

  204. Castro S, Fernandez JJ, Vicente R, Fananas FJ, Rodriguez F (2012) Chem Commun 48:9089

    Article  CAS  Google Scholar 

  205. Wen J, Zhang R-Y, Chen S-Y, Zhang J, Yu X-Q (2012) J Org Chem 77:766

    Article  CAS  Google Scholar 

  206. Ozanne-Beaudenon A, Quideau S (2005) Angew Chem Int Ed 44:7065

    Article  CAS  Google Scholar 

  207. Kang S-K, Lee H-W, Jang S-B, Ho P-S (1996) J Org Chem 61:4720

    Article  CAS  Google Scholar 

  208. Kang S-K, Yamaguchi T, Kim T-H, Ho P-S (1996) J Org Chem 61:9082

    Article  CAS  Google Scholar 

  209. Xiao B, Fu Y, Xu J, Gong T-J, Dai J-J, Yi J, Liu L (2010) J Am Chem Soc 132:468

    Article  CAS  Google Scholar 

  210. Uhlig N, Li C-J (2014) Chem Eur J 20:12066

    Article  CAS  Google Scholar 

  211. Bedford RB, Mitchell CJ, Webster RL (2010) Chem Commun 46:3095

    Article  CAS  Google Scholar 

  212. Chan LY, Cheong L, Kim S (2013) Org Lett 15:2186

    Article  CAS  Google Scholar 

  213. Chary BC, Kim S, Park Y, Kim J, Lee PH (2013) Org Lett 15:2692

    Article  CAS  Google Scholar 

  214. Wu Z, Chen S, Hu C, Li Z, Xiang H, Zhou X (2013) ChemCatChem 5:2839

    Article  CAS  Google Scholar 

  215. Hu R-B, Zhang H, Zhang X-Y, Yang S-D (2014) Chem Commun 50:2193

    Article  CAS  Google Scholar 

  216. Neufeldt SR, Sanford MS (2012) Adv Synth Catal 354:3517

    Article  CAS  Google Scholar 

  217. Ciana C-L, Phipps RJ, Brandt JR, Meyer F-M, Gaunt MJ (2011) Angew Chem Int Ed 50:458

    Article  CAS  Google Scholar 

  218. Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ (2011) Angew Chem Int Ed 50:463

    Article  CAS  Google Scholar 

  219. Deprez NR, Kalyani D, Krause A, Sanford MS (2006) J Am Chem Soc 128:4972

    Article  CAS  Google Scholar 

  220. Malmgren J, Nagendiran A, Tai C-W, Bäckvall J-E, Olofsson B (2014) Chem Eur J 20:13531

    Article  CAS  Google Scholar 

  221. Zhu Y, Bauer M, Ackermann L (2015) Chem Eur J. doi:10.1002/chem.201501831

    Google Scholar 

  222. Wagner AM, Sanford MS (2011) Org Lett 13:288

    Article  CAS  Google Scholar 

  223. Pitts AK, O’Hara F, Snell RH, Gaunt MJ (2015) Angew Chem Int Ed 54:5451

    Article  CAS  Google Scholar 

  224. Modha SG, Greaney MF (2015) J Am Chem Soc 137:1416

    Article  CAS  Google Scholar 

  225. Wu Y, Peng X, Luo B, Wu F, Liu B, Song F, Huang P, Wen S (2014) Org Biomol Chem 12:9777

    Article  CAS  Google Scholar 

  226. Klapars A, Antilla JC, Huang X, Buchwald SL (2001) J Am Chem Soc 123:7727

    Article  CAS  Google Scholar 

  227. Kieffer ME, Chuang KV, Reisman SE (2013) J Am Chem Soc 135:5557

    Article  CAS  Google Scholar 

  228. Kieffer ME, Chuang KV, Reisman SE (2012) Chem Sci 3:3170

    Article  CAS  Google Scholar 

  229. Liu C, Zhang W, Dai L-X, You S-L (2012) Org Lett 14:4525

    Article  CAS  Google Scholar 

  230. Liu C, Zhang W, Dai L-X, You S-L (2014) Chem Asian J 9:2113

    Article  CAS  Google Scholar 

  231. Tang D-TD, Collins KD, Ernst JB, Glorius F (2014) Angew Chem Int Ed 53:1809

    Article  CAS  Google Scholar 

  232. Hickman AJ, Sanford MS (2011) ACS Catal 1:170

    Article  CAS  Google Scholar 

  233. Wagner AM, Hickman AJ, Sanford MS (2013) J Am Chem Soc 135:15710

    Article  CAS  Google Scholar 

  234. Park T-H, Hickman AJ, Koh K, Martin S, Wong-Foy AG, Sanford MS, Matzger AJ (2011) J Am Chem Soc 133:20138

    Article  CAS  Google Scholar 

  235. Collins KD, Honeker R, Vasquez-Cespedes S, Tang D-TD, Glorius F (2015) Chem Sci 6:1816

    Article  CAS  Google Scholar 

  236. Storr TE, Greaney MF (2013) Org Lett 15:1410

    Article  CAS  Google Scholar 

  237. Kang S-K, Lee H-W, Jang S-B, Ho P-S (1996) Chem Commun 835

    Google Scholar 

  238. Kang S-K, Yoon S-K, Kim Y-M (2001) Org Lett 3:2697

    Article  CAS  Google Scholar 

  239. Kang SK, Lim KH, Ho PS, Kim WY (1997) Synthesis 874

    Google Scholar 

  240. Tang S, Peng P, Zhong P, Li J-H (2008) J Org Chem 73:5476

    Article  CAS  Google Scholar 

  241. Suarez LL, Greaney MF (2011) Chem Commun 47:7992

    Article  CAS  Google Scholar 

  242. Sinai Á, Mészáros Á, Gáti T, Kudar V, Palló A, Novák Z (2013) Org Lett 15:5654

    Article  CAS  Google Scholar 

  243. Walkinshaw AJ, Xu W, Suero MG, Gaunt MJ (2013) J Am Chem Soc 135:12532

    Article  CAS  Google Scholar 

  244. Peng J, Chen C, Chen J, Su X, Xi C, Chen H (2014) Org Lett 16:3776

    Article  CAS  Google Scholar 

  245. Zhang F, Das S, Walkinshaw AJ, Casitas A, Taylor M, Suero MG, Gaunt MJ (2014) J Am Chem Soc 136:8851

    Article  CAS  Google Scholar 

  246. Chen J, Chen C, Chen J, Wang G, Qu H (2015) Chem Commun 51:1356

    Article  CAS  Google Scholar 

  247. Collins BSL, Suero MG, Gaunt MJ (2013) Angew Chem Int Ed 52:5799

    Article  CAS  Google Scholar 

  248. Li W, Zhang J (2010) Chem Commun 46:8839

    Article  CAS  Google Scholar 

  249. Zhu D, Wu Y, Wu B, Luo B, Ganesan A, Wu F-H, Pi R, Huang P, Wen S (2014) Org Lett 16:2350

    Article  CAS  Google Scholar 

  250. Kang S-K, Lee H-W, Jang S-B, Kim T-H, Pyun S-J (1996) J Org Chem 61:2604

    Article  CAS  Google Scholar 

  251. Kang S-K, Ho P-S, Yoon S-K, Lee J-C, Lee K-J (1998) Synthesis 823

    Google Scholar 

  252. Nasir Baig RB, Varma RS (2013) Green Chem 15:398

    Article  CAS  Google Scholar 

  253. Gigant N, Chausset-Boissarie LT, Belhomme M-C, Poisson T, Pannecoucke X, Gillaizeau I (2013) Org Lett 15:278

    Article  CAS  Google Scholar 

  254. Baralle A, Fensterbank L, Goddard J-P, Ollivier C (2013) Chem Eur J 19:10809

    Article  CAS  Google Scholar 

  255. Fumagalli G, Boyd S, Greaney MF (2013) Org Lett 15:4398

    Article  CAS  Google Scholar 

  256. Hopkinson MN, Sahoo B, Glorius F (2014) Adv Synth Catal 356:2794

    Article  CAS  Google Scholar 

  257. Phipps RJ, McMurray L, Ritter S, Duong HA, Gaunt MJ (2012) J Am Chem Soc 134:10773

    Article  CAS  Google Scholar 

  258. Zhou B, Hou W, Yang Y, Feng H, Li Y (2014) Org Lett 16:1322

    Article  CAS  Google Scholar 

  259. Shi L, Wang Y, Yang H, Fu H (2014) Org Biomol Chem 12:4070

    Article  CAS  Google Scholar 

  260. Cahard E, Bremeyer N, Gaunt MJ (2013) Angew Chem Int Ed 52:9284

    Article  CAS  Google Scholar 

  261. Cahard E, Male HPJ, Tissot M, Gaunt MJ (2015) J Am Chem Soc 137:7986

    Article  CAS  Google Scholar 

  262. Kang S-K, Yamaguchi T, Ho P-S, Kim W-Y, Ryu H-C (1998) J Chem Soc Perkin Trans 1 841

    Google Scholar 

  263. Wang D, Ge B, Li L, Shan J, Ding Y (2014) J Org Chem 79:8607

    Article  CAS  Google Scholar 

  264. Pan F, Shen P-X, Zhang L-S, Wang X, Shi Z-J (2013) Org Lett 15:4758

    Article  CAS  Google Scholar 

  265. Iyanaga M, Aihara Y, Chatani N (2014) J Org Chem 79:11933

    Article  CAS  Google Scholar 

  266. Jiang H, Cheng Y, Wang R, Zhang Y, Yu S (2014) Chem Commun 50:6164

    Article  CAS  Google Scholar 

  267. Kitamura T, Yamane M (1995) J Chem Soc Chem Commun 983

    Google Scholar 

  268. Kitamura T, Yamane M, Inoue K, Todaka M, Fukatsu N, Meng Z, Fujiwara Y (1999) J Am Chem Soc 121:11674

    Article  CAS  Google Scholar 

  269. Dudnik AS, Chernyak N, Huang C, Gevorgyan V (2010) Angew Chem Int Ed 49:8729

    Article  CAS  Google Scholar 

  270. Vase KH, Holm AH, Norrman K, Pedersen SU, Daasbjerg K (2007) Langmuir 23:3786

    Article  CAS  Google Scholar 

  271. Chan CK, Beechem TE, Ohta T, Brumbach MT, Wheeler DR, Stevenson KJ (2013) J Phys Chem C 117:12038

    Article  CAS  Google Scholar 

  272. Hof F, Schäfer RA, Weiss C, Hauke F, Hirsch A (2014) Chem Eur J 20:16644

    Article  CAS  Google Scholar 

  273. Stevenson KJ, Veneman PA, Gearba RI, Mueller KM, Holliday BJ, Ohta T, Chan CK (2014) Faraday Disc 172:273

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, 106 91, Stockholm, Sweden

    Berit Olofsson

  2. Stellenbosch Institute for Advanced Study (STIAS), Wallenberg Research Centre at Stellenbosch University, Marais Street, Stellenbosch, 7600, South Africa

    Berit Olofsson

Authors
  1. Berit Olofsson
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Berit Olofsson .

Editor information

Editors and Affiliations

  1. School of Chemistry, Cardiff University , Cardiff, United Kingdom

    Thomas Wirth

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Olofsson, B. (2015). Arylation with Diaryliodonium Salts. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 373. Springer, Cham. https://doi.org/10.1007/128_2015_661

Download citation

Publish with us

Policies and ethics

Search

Navigation