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C-C-Bond Forming Reactions

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Hypervalent Iodine Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 224))

Abstract

The use of hypervalent iodine reagents in carbon-carbon bond forming reactions is summarized with particular emphasis on applications in organic synthesis. The most important recent methods involve the radical decarboxylative alkylation of organic substrates with [bis(acyloxy)iodo]arenes, spirocyclization of para- and ortho-substituted phenols, the intramolecular oxidative coupling of phenol ethers, and the reactions of iodonium salts and ylides. A significant recent research activity is centered in the area of the transition metalmediated coupling reactions of the alkenyl-, aryl-, and alkynyliodonium salts.

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References

  1. Moriarty RM, Vaid RK (1990) Synthesis 431

    Google Scholar 

  2. Wirth T, Hirt UH (1999) Synthesis 1271

    Google Scholar 

  3. Muraki T, Togo H, Yokoyama M (1997) Rev Heteroatom Chem 17:213

    CAS  Google Scholar 

  4. Zhdankin VV, Stang PJ (1998) Tetrahedron 54:10927

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  6. Kitamura T, Fujiwara Y (1997) Org Prep Proced Int 29:409

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  8. Umemoto T (1996) Chem Rev 96:1757

    CAS  Google Scholar 

  9. Varvoglis A (1992) The Organic Chemistry of Polycoordinated Iodine. VCH, New York

    Google Scholar 

  10. Varvoglis A (1997) Hypervalent Iodine in Organic Synthesis. Academic Press, London

    Google Scholar 

  11. Togo H, Aoki M, Yokoyama M (1991) Tetrahedron Lett 32:6559

    CAS  Google Scholar 

  12. Togo H, Aoki M, Kuramochi T, Yokoyama M (1993) J Chem Soc, Perkin Trans 1 2417

    Google Scholar 

  13. Vismara E, Torri G, Pastori N, Marchiandi M (1992) Tetrahedron Lett 33:7575

    CAS  Google Scholar 

  14. Togo H, Aoki M, Yokoyama M (1991) Chem Lett 1691

    Google Scholar 

  15. Togo H, Aoki M, Yokoyama M (1992) Chem Lett 2169

    Google Scholar 

  16. Togo H, Aoki M, Yokoyama M (1993) Tetrahedron 49:8241

    CAS  Google Scholar 

  17. Mowbray CE, Pattenden G (1993) Tetrahedron Lett 34:127

    CAS  Google Scholar 

  18. Kurti L, Herczegh P, Visy J, Simonyi M, Antus S, Pelter A (1999) J Chem Soc Perkin Trans 1:379

    Google Scholar 

  19. Swenton JS, Callinan A, Chen Y, Rohde JJ, Kerns ML, Morrow GW (1996) J Org Chem 61:1267

    CAS  Google Scholar 

  20. Wells G, Seaton A, Stevens MFG (2000) J Med Chem 43:1550

    CAS  Google Scholar 

  21. Kita Y, Arisawa M, Gyoten M, Nakajima M, Hamada R, Tohma H, Takada T (1998) J Org Chem 63:6625

    CAS  Google Scholar 

  22. Quideau S, Looney MA, Pouysegu L (1999) Org Lett 1:1651

    CAS  Google Scholar 

  23. Kita Y, Takada T, Ibaraki M, Gyoten M, Mihara S, Fujita S, Tohma H (1996) J Org Chem 61:223

    CAS  Google Scholar 

  24. Kita Y, Takada T, Gyoten M, Tohma H, Zenk MH, Eichhorn J (1996) J Org Chem 61:5857

    CAS  Google Scholar 

  25. Asmanidou A, Papoutsis I, Spyroudis S, Varvoglis A (2000) Molecules 5:874

    CAS  Google Scholar 

  26. Ward RS, Pelter A, Abd-El-Ghani A (1996) Tetrahedron 52:1303

    CAS  Google Scholar 

  27. Tohma H, Morioka H, Takizawa S, Arisawa M, Kita Y (2001) Tetrahedron 57:345

    CAS  Google Scholar 

  28. Kita Y, Gyoten M, Ohtsubo M, Tohma H, Takada T (1996) J Chem Soc Chem Commun 1481

    Google Scholar 

  29. Takada T, Arisawa M, Gyoten M, Hamada R, Tohma H, Kita Y (1998) J Org Chem 63: 7698

    CAS  Google Scholar 

  30. Arisawa M, Ramesh NG, Nakajima M, Tohma H, Kita Y (2001) J Org Chem 66:59

    CAS  Google Scholar 

  31. Olivera R, SanMartin R, Pascual S, Herrero M, Dominguez E (1999) Tetrahedron Lett 40:3479

    CAS  Google Scholar 

  32. Moreno I, Tellitu I, SanMartin R, Badia D, Carrillo L, Dominguez E (1999) Tetrahedron Lett 40:5067

    CAS  Google Scholar 

  33. Zhdankin VV (1997) Rev Heteroatom Chem 17:133

    CAS  Google Scholar 

  34. Zhdankin VV, Kuehl CJ, Krasutsky AP, Bolz JT, Mismash B, Woodward JK, Simonsen AJ (1995) Tetrahedron Lett 36:7975

    CAS  Google Scholar 

  35. Zhdankin VV, Kuehl CJ, Arif AM, Stang PJ (1996) Mendeleev Commun 50

    Google Scholar 

  36. Akai S, Okuno T, Takada T, Tohma H, Kita Y (1996) Heterocycles 42:47

    CAS  Google Scholar 

  37. Shaffer CL, Morton MD, Hanzlik RP (2001) J Am Chem Soc 123:349

    CAS  Google Scholar 

  38. Kuehl CJ, Bolz JT, Zhdankin VV (1995) Synthesis 312

    Google Scholar 

  39. Zhdankin VV, Kuehl CJ, Simonsen AJ (1996) J Org Chem 61:8272

    CAS  Google Scholar 

  40. Zhdankin VV, Tykwinski R, Mullikin M, Berglund B, Caple R, Zefirov NS, Kozmin AS (1989) J Org Chem 54:2605

    CAS  Google Scholar 

  41. Zhdankin VV, Erickson SA, Hanson KJ (1997) J Am Chem Soc 119:4775

    CAS  Google Scholar 

  42. Ochiai M (1999) In: Akiba K (ed) Chemistry of Hypervalent Compounds. VCH, New York, p 327

    Google Scholar 

  43. Ochiai M (2000) J Organomet Chem 611:494

    CAS  Google Scholar 

  44. Okuyama T (1999) Rev Heteroatom Chem 21:257

    CAS  Google Scholar 

  45. Pirkuliev NS, Brel VK, Zefirov NS (2000) Russ Chem Rev 69:105

    CAS  Google Scholar 

  46. Ochiai M, Takaoka Y, Nagao Y (1988) J Am Chem Soc 110:6565

    CAS  Google Scholar 

  47. Ochiai M, Sueda T, Uemura K, Masaki Y (1995) J Org Chem 60:2624

    CAS  Google Scholar 

  48. Ochiai M, Kunishima M, Tani S, Nagao Y (1991) J Am Chem Soc 113:3135

    CAS  Google Scholar 

  49. Ochiai M, Uemura K, Masaki Y (1993) J Am Chem Soc 115:2528

    CAS  Google Scholar 

  50. Ochiai M, Shu T, Nagaoka T, Kitagawa Y (1997) J Org Chem 62:2130

    CAS  Google Scholar 

  51. Papoutsis I, Spyroudis S, Varvoglis A (1998) Tetrahedron 54:1005

    CAS  Google Scholar 

  52. Stang PJ, Schwartz A, Blume T, Zhdankin VV (1992) Tetrahedron Lett 33:6759

    CAS  Google Scholar 

  53. Stang PJ, Blume T, Zhdankin VV (1993) Synthesis 35

    Google Scholar 

  54. Ochiai M, Sumi K, Takaoka Y, Kunishima Y, Nagao Y, Shiro M, Fujita E (1998) Tetrahedron 44:4095

    Google Scholar 

  55. Hinkle RJ, Leri AC, David GA, Erwin WM (2000) Org Lett 2:1521

    CAS  Google Scholar 

  56. Kang SK, Yamaguchi T, Kim TH, Ho PS (1996) J Org Chem 61:9082

    CAS  Google Scholar 

  57. Huang X, Xu XH (1998) J Chem Soc Perkin Trans 1 3321

    Google Scholar 

  58. Kang SK, Yoon SK, Kim YM (2001) Org Lett 3:2697

    CAS  Google Scholar 

  59. Pirguliyev NS, Brel VK, Zefirov NS, Stang PJ (1999) Tetrahedron 55:12377

    CAS  Google Scholar 

  60. Hinkle RJ, Poulter GT, Stang PJ (1993) J Am Chem Soc 115:11626

    CAS  Google Scholar 

  61. Ryan JH, Stang PJ (1996) J Org Chem 61:6162

    CAS  Google Scholar 

  62. Fraysse S, Coudret C, Launay JP (2000) Eur J Inorg Chem 1581

    Google Scholar 

  63. Moriarty RM, Epa WR, Awasthi AK (1991) J Am Chem Soc 113:6315

    CAS  Google Scholar 

  64. Yoshida M, Hara S, Fukuhara T, Yoneda N (2000) Tetrahedron Lett 41:3887

    CAS  Google Scholar 

  65. Kurihara Y, Sodeoka M, Shibasaki M (1994) Chem Pharm Bull 42:2357

    CAS  Google Scholar 

  66. Moriarty RM, Epa WR (1992) Tetrahedron Lett 33:4095

    CAS  Google Scholar 

  67. Roh KR, Kim JY, Kim YH (1999) Tetrahedron Lett 40:1903

    CAS  Google Scholar 

  68. Hara S, Yamamoto K, Yoshida M, Fukuhara T, Yoneda N (1999) Tetrahedron Lett 40:7815

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  72. Iwama T, Birman VB, Kozmin SA, Rawal VH (1999) Org Lett 1:673

    CAS  Google Scholar 

  73. Ryan JH, Stang PJ (1997) Tetrahedron Lett 38:5061

    CAS  Google Scholar 

  74. Chen DW, Ochiai M (1999) J Org Chem 64:6804

    CAS  Google Scholar 

  75. Bumagin NA, Sukhomlinova LI, Banchikov AN, Tolstaya TP, Beletskaya IP (1992) Russ Chem Bull 41:2130

    Google Scholar 

  76. Bumagin NA, Sukhomlinova LI, Igushkina SO, Banchikov AN, Tolstaya TP, Beletskaya IP (1992) Russ Chem Bull 41:2128

    Google Scholar 

  77. Bumagin NA, Luzikova EV, Sukhomlinova LI, Tolstaya TP, Beletskaya IP (1995) Russ Chem Bull 44:385

    Google Scholar 

  78. Luzikova EV, Sukhomlinova LI, Tolstaya TP, Bumagin NA, Beletskaya IP (1995) Russ Chem Bull 44:556

    Google Scholar 

  79. Kang SK, Lee HW, Jang SB, Ho PS (1996) J Org Chem 61:4720

    CAS  Google Scholar 

  80. Xia M, Chen ZC (1999) Synth Commun 29:2457

    CAS  Google Scholar 

  81. Bumagin NA, Tsarev DA (1998) Tetrahedron Lett 39:8155

    CAS  Google Scholar 

  82. Al-Qahtani MH, Pike VW (2000) J Chem Soc Perkin Trans 1 1033

    Google Scholar 

  83. Kang SK, Lee YT, Lee SH (1999) Tetrahedron Lett 40:3573

    CAS  Google Scholar 

  84. Kang SK, Ho PS, Yoon SK, Lee JC, Lee KJ (1998) Synthesis 823

    Google Scholar 

  85. Kang SK, Yamaguchi T, Ho PS, Kim WY, Yoon SK (1997) Tetrahedron Lett 38:1947

    CAS  Google Scholar 

  86. Kang SK, Yamaguchi T, Hong RK, Kim TH, Pyung SJ (1997) Tetrahedron 53:3027

    CAS  Google Scholar 

  87. Kang SK, Choi SC, Baik TG (1999) Synth Commun 29:2493

    CAS  Google Scholar 

  88. Kang SK, Ryu HC, Kim JW (2001) Synth Commun 31:1021

    CAS  Google Scholar 

  89. Huang X, Sun AM (1998) Synth Commun 28:773

    CAS  Google Scholar 

  90. Kang SK, Yamaguchi T, Ho PS, Kim WY, Ryu HC (1998) J Chem Soc Perkin Trans 1 841

    Google Scholar 

  91. Kang SK, Lee HW, Jang SB, Kim TH, Pyung SJ (1996) J Org Chem 61:260

    Google Scholar 

  92. Kang SK, Baik TG, Hur Y (1999) Tetrahedron 55:6863

    CAS  Google Scholar 

  93. Xia M, Chen ZC (2000) Synth Commun 30:1281

    CAS  Google Scholar 

  94. Wang L, Chen ZC (2000) Synth Commun 30:3607

    CAS  Google Scholar 

  95. Kang SK, Yamaguchi T, Kim JS, Choi SC, Ahn C (1997) Synth Commun 27:1105

    CAS  Google Scholar 

  96. Liang Y, Luo S, Liu C, Wu X, Ma Y (2000) Tetrahedron 56:2961

    CAS  Google Scholar 

  97. Kang SK, Kim JS, Choi SC, Lim KH (1998) Synthesis 1249

    Google Scholar 

  98. Kang SK, Yoon SK, Lim KH, Son HJ, Baik TG (1998) Synth Commun 28:3645

    CAS  Google Scholar 

  99. Bumagin NA, Sukhomlinova LI, Luzikova EV, Tolstaya TP, Beletskaya IP (1996) Tetrahedron Lett 37:897

    CAS  Google Scholar 

  100. Kang SK, Lee HW, Jang SB, Ho PS (1996) J Chem Soc Chem Commun 835

    Google Scholar 

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

    Google Scholar 

  102. Radhakrishnan U, Stang PJ (2001) Org Lett 3:859

    CAS  Google Scholar 

  103. Kang SK, Kim WY, Lee YT, Ahn SK, Kim JC (1998) Tetrahedron Lett 39:2131

    CAS  Google Scholar 

  104. Kang SK, Ryu HC, Lee SW (1999) J Chem Soc Perkin Trans 1 2661

    Google Scholar 

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

    CAS  Google Scholar 

  106. Okuma K, Yamamoto T, Shirokawa T, Kitamura T, Fujiwara Y (1996) Tetrahedron Lett 37:8883

    CAS  Google Scholar 

  107. Kitamura T, Fukatsu N, Fujiwara Y (1998) J Org Chem 63:8579

    CAS  Google Scholar 

  108. Kitamura T, Meng Z, Fujiwara Y (2000) Tetrahedron Lett 41:6611

    CAS  Google Scholar 

  109. Ochiai M, Ito T, Takaoka Y, Masaki Y, Kunishima M, Tani S, Nagao Y (1990) J Chem Soc Chem Commun 118

    Google Scholar 

  110. Suzuki T, Uozumi Y, Shibasaki M (1991) J Chem Soc Chem Commun 1593

    Google Scholar 

  111. Bachi MD, Bar-Ner N, Crittell CM, Stang PJ, Williamson BL (1991) J Org Chem 56:3912

    CAS  Google Scholar 

  112. Bachi MD, Bar-Ner N, Stang PJ, Williamson BL (1993) J Org Chem 58:7923

    CAS  Google Scholar 

  113. Stang PJ, Kitamura T (1991) Org Syn 70:215

    Google Scholar 

  114. Kitamura T, Tanaka T, Taniguchi H, Stang PJ (1991) J Chem Soc Perkin Trans 1 2892

    Google Scholar 

  115. Kitamura T, Lee CH, Taniguchi Y, Fujiwara Y, Matsumoto M, Sano YF (1997) J Am Chem Soc 119:619

    CAS  Google Scholar 

  116. Eaton PA, Gallopini E, Gilardi R (1994) J Am Chem Soc 116:7588

    CAS  Google Scholar 

  117. Sun AM, Huang XJ (1998) Chem Res Synop 616

    Google Scholar 

  118. Huang X, Zhong P (1999) J Chem Soc Perkin Trans 1 1543

    Google Scholar 

  119. Sun AM, Huang X (1999) Tetrahedron 55:13201

    CAS  Google Scholar 

  120. Kitamura T, Mihara I, Taniguchi H, Stang PJ (1990) J Chem Soc Chem Commun 614

    Google Scholar 

  121. Ochiai M, Kunishima M, Nagao Y, Fuji K, Shiro M, Fujita E (1986) J Am Chem Soc 108:8281

    CAS  Google Scholar 

  122. Tykwinski RR, Stang PJ, Persky NE (1994) Tetrahedron Lett 35:23

    CAS  Google Scholar 

  123. Kitamura T, Stang PJ (1988) Tetrahedron Lett 29:1887

    CAS  Google Scholar 

  124. Tykwinski RR, Whiteford JA, Stang PJ (1993) J Chem Soc Chem Commun 1800

    Google Scholar 

  125. Williamson BL, Tykwinski R, Stang PJ (1994) J Am Chem Soc 116:93

    CAS  Google Scholar 

  126. Kitamura T, Zheng L, Fukuoka T, Fujiwara Y, Taniguchi H, Sakurai M, Tanaka R (1997) J Chem Soc Perkin Trans 2 1511

    Google Scholar 

  127. Nikas S, Rodios N, Varvoglis A (2000) Molecules 5:1182

    CAS  Google Scholar 

  128. Kitamura T, Tsuda K, Fujiwara Y (1998) Tetrahedron Lett 39:5375

    CAS  Google Scholar 

  129. Feldman KS, Bruendl MM (1998) Tetrahedron Lett 39:2911

    CAS  Google Scholar 

  130. Feldman KS, Wrobleski ML (2000) J Org Chem 65:8659

    CAS  Google Scholar 

  131. Feldman KS, Bruendl MM, Schildknegt K, Bohnstedt AC (1996) J Org Chem 61:5440

    CAS  Google Scholar 

  132. Feldman KS, Bruendl MM, Schildknegt K (1995) J Org Chem 60:7722

    CAS  Google Scholar 

  133. Feldman KS, Mareska DA (1998) J Am Chem Soc 120:4027

    CAS  Google Scholar 

  134. Feldman KS, Mareska DA (1999) J Org Chem 64:5650

    CAS  Google Scholar 

  135. Feldman KS, Mingo PA, Hawkins PCD (1999) Heterocycles 51:1283

    CAS  Google Scholar 

  136. Schildknegt K, Bohnstedt AC, Feldman KS, Sambandam A (1995) J Am Chem Soc 117:7544

    CAS  Google Scholar 

  137. Williamson BL, Stang PJ, Arif AM (1993) J Am Chem Soc 115:2590

    CAS  Google Scholar 

  138. Murch P, Arif AM, Stang PJ (1997) J Org Chem 62:5959

    CAS  Google Scholar 

  139. Stang PJ, Zhdankin VV (1991) J Am Chem Soc 113:4571

    CAS  Google Scholar 

  140. Camacho MB, Clark AE, Liebrecht TA, DeLuca JP (2000) J Am Chem Soc 122:5210

    CAS  Google Scholar 

  141. Zhu S, Chen Q, Kuang W (1993) J Fluorine Chem 60:39

    CAS  Google Scholar 

  142. Zhu S (1994) Heteroatom Chem 5:9

    CAS  Google Scholar 

  143. Hackenberg J, Hanack M (1991) J Chem Soc Chem Commun 470

    Google Scholar 

  144. Müller P, Fernandez D (1995) Helv Chim Acta 78:947

    Google Scholar 

  145. Fairfax DJ, Austin DJ, Xu SL, Padwa A (1992) J Chem Soc Perkin Trans 1 2837

    Google Scholar 

  146. Moriarty RM, Kim J, Guo L (1993) Tetrahedron Lett 34:4129

    CAS  Google Scholar 

  147. Moriarty RM, May EJ, Prakash O (1997) Tetrahedron Lett 38:4333

    CAS  Google Scholar 

  148. Moriarty RM, May EJ, Guo L, Prakash O (1998) Tetrahedron Lett 39:765

    CAS  Google Scholar 

  149. Muller P, Fernandez D, Nury P, Rossier JC (1998) J Phys Org Chem 11:321

    CAS  Google Scholar 

  150. Muller P, Bolea C (2000) Synlett 826

    Google Scholar 

  151. Muller P, Bolea C (2001) Molecules 6:258

    CAS  Google Scholar 

  152. Muller P, Bolea C (2001) Helv Chim Acta 84:1093

    CAS  Google Scholar 

  153. Kobayashi K, Uneda T, Kawakita M, Morikawa O, Konishi H (1997) Tetrahedron Lett 38:837

    CAS  Google Scholar 

  154. Asouti A, Hadjiarapoglou LP (1998) Tetrahedron Lett 39:9073

    CAS  Google Scholar 

  155. Alexiou I, Gogonas EP, Hadjiarapoglou LP (1999) Synlett 1925

    Google Scholar 

  156. Gogonas EP, Hadjiarapoglou LP (2000) Tetrahedron Lett 41:9299

    CAS  Google Scholar 

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Zhdankin, V.V. (2003). C-C-Bond Forming Reactions. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 224. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46114-0_4

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