Skip to main content

Gold-Catalyzed O–H Bond Addition to Unsaturated Organic Molecules

  • Chapter
  • First Online:
Hydrofunctionalization

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 43))

Abstract

In this chapter, we review the synthetic and mechanistic aspects of addition reactions of water and alcohols to alkynes, alkenes, and allenes in the presence of gold catalysts. In addition, gold-catalyzed hydroxy- and alkoxycyclizations of 1, n-enynes (n = 5–7) are also covered.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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. Hashmi ASK (2007) Chem Rev 107:3180–3211

    CAS  Google Scholar 

  2. Jiménez-Núñez E, Echavarren AM (2007) Chem Commun 333–346

    Google Scholar 

  3. Jiménez-Núñez E, Echavarren AM (2008) Chem Rev 108:3326–3350

    Google Scholar 

  4. Zhang L, Sun J, Kozmin SA (2006) Adv Synth Catal 348:2271–2296

    CAS  Google Scholar 

  5. Fürstner A, Davies PW (2007) Angew Chem Int Ed Engl 46:3410–3449

    Google Scholar 

  6. Fürstner A (2009) Chem Soc Rev 38:3208

    Google Scholar 

  7. Gorin DJ, Toste FD (2007) Nature 446:395–403

    CAS  Google Scholar 

  8. Michelet V, Toullec PY, Genêt J-P (2008) Angew Chem Int Ed Engl 47:4268–4315

    CAS  Google Scholar 

  9. Sohel SMA, Liu R-S (2009) Chem Soc Rev 38:2269–2281

    Google Scholar 

  10. Belmont P, Parker E (2009) Eur J Org Chem 6075–6089

    Google Scholar 

  11. Hashmi ASK, Rudolph M (2008) Chem Soc Rev 37:1766–1775

    CAS  Google Scholar 

  12. Shen HC (2008) Tetrahedron 64:7847–7870

    CAS  Google Scholar 

  13. Shapiro ND, Toste FD (2010) Synlett:675–691

    Google Scholar 

  14. Pyykkö P (2002) Angew Chem Int Ed Engl 41:3573–3578

    Google Scholar 

  15. Pyykkö P (2004) Angew Chem Int Ed Engl 43:4412–4456

    Google Scholar 

  16. Schwartz H (2003) Angew Chem Int Ed Engl 42:4442–4454

    Google Scholar 

  17. Akana JA, Bhattacharyya KX, Müller P, Sadighi JP (2007) J Am Chem Soc 129:7736–7737

    CAS  Google Scholar 

  18. Flügge S, Anoop A, Goddard R, Thiel W, Fürstner A (2009) Chem Eur J 15:8558–8565

    Google Scholar 

  19. Wittig G, Fischer S (1972) Chem Ber 105:3542–3552

    CAS  Google Scholar 

  20. Lavallo V, Frey GD, Kousar S, Donnadieu B, Bertrand G (2007) Proc Natl Acad Sci USA 104:13569–13573

    CAS  Google Scholar 

  21. Shapiro ND, Toste FD (2008) Proc Natl Acad Sci USA 105:2779–2782

    CAS  Google Scholar 

  22. Zuccaccia D, Belpassi L, Rocchigiani L, Tarantelli L, Macchioni A (2010) Inorg Chem 49:3080–3082

    CAS  Google Scholar 

  23. Huettel R, Forkl H (1972) Chem Ber 105:1664–1673

    CAS  Google Scholar 

  24. Schulte P, Behrens U (1998) Chem Commun 1633–1634

    Google Scholar 

  25. Brown TJ, Widenhoefer RA (2011) J Organomet Chem 696:1216–1220

    CAS  Google Scholar 

  26. Schmidbaur H, Schier A (2010) Organometallics 29:2–23

    CAS  Google Scholar 

  27. Rasika Dias HV, Wu J (2008) Eur J Inorg Chem 509–522

    Google Scholar 

  28. Rasika Dias HV, Wu J (2007) Angew Chem Int Ed Engl 46:7814–7816

    Google Scholar 

  29. Rasika Dias HV, Fianchini M, Cundari TR, Campana CF (2008) Angew Chem Int Ed Engl 47:556–559

    Google Scholar 

  30. Cinellu MA, Minghetti G, Stoccoro S, Zucca A, Manassero M (2004) Chem Commun 1618–1619

    Google Scholar 

  31. Cinellu MA, Minghetti G, Cocco F, Stoccoro S, Zucca A, Manassero M, Arca M (2006) Dalton Trans 5703–5716

    Google Scholar 

  32. Komiya S, Kochi JK (1977) J Organomet Chem 135:65–72

    CAS  Google Scholar 

  33. Roulet R, Favez R (1975) Chimia 29:346–348

    CAS  Google Scholar 

  34. Uson R, Laguna A, Sanjoaquin JL (1974) J Organomet Chem 80:147–154

    CAS  Google Scholar 

  35. Tauchner P, Huettel R (1974) Chem Ber 107:3761–3770

    CAS  Google Scholar 

  36. Leedham TJ, Powell DB, Scott JGV (1973) Spectrochim Acta A 29:559–565

    CAS  Google Scholar 

  37. Huettel R, Tauchner P, Forkl H (1972) Chem Ber 105:1–7

    CAS  Google Scholar 

  38. Brown TJ, Dickens MG, Widenhoefer RA (2009) Chem Commun 6451–6453

    Google Scholar 

  39. Brown TJ, Dickens MG, Widenhoefer RA (2009) J Am Chem Soc 131:6350–6351

    CAS  Google Scholar 

  40. Hooper TN, Green M, McGrady JE, Patel JR, Russell CA (2009) Chem Commun 3877–3879

    Google Scholar 

  41. Hooper TN, Butts CP, Green M, Haddow MF, McGrady JE, Russell CA (2009) Chem Eur J 15:12196–12200

    CAS  Google Scholar 

  42. García-Mota M, Cabello N, Maseras F, Echavarren AM, Pérez-Ramírez J, López N (2008) ChemPhysChem 11:1624

    Google Scholar 

  43. Zuccaccia D, Belpassi L, Tarantelli F, Macchioni A (2009) J Am Chem Soc 131:3170–3171

    CAS  Google Scholar 

  44. Salvi N, Belpassi L, Zuccaccia D, Tarantelli F, Macchioni A (2010) J Organomet Chem 695:2679–2686

    CAS  Google Scholar 

  45. Brown TJ, Sugie A, Dickens MG, Widenhoefer RA (2010) Organometallics 29:4207–4209

    CAS  Google Scholar 

  46. Brooner REM, Widenhoefer RA (2011) Organometallics 30:3182–3193

    CAS  Google Scholar 

  47. Morita N, Krause N (2006) Angew Chem Int Ed Engl 45:1897–1899

    CAS  Google Scholar 

  48. Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM (2004) Angew Chem Int Ed Engl 43:2402–2406

    CAS  Google Scholar 

  49. Ferrer C, Raducan M, Nevado C, Claverie CK, Echavarren AM (2007) Tetrahedron 63:6306–6316

    CAS  Google Scholar 

  50. Teles JH, Brode S, Chabanas M (1998) Angew Chem Int Ed Engl 37:1415–1418

    CAS  Google Scholar 

  51. Mizushima E, Sato K, Hayashi T, Tanaka M (2002) Angew Chem Int Ed Engl 41:4563–4565

    CAS  Google Scholar 

  52. Mizushima E, Hayashi T, Tanaka M (2003) Org Lett 5:3349–3352

    CAS  Google Scholar 

  53. Yang Y, Ramamoorthy V, Sharp PR (1993) Inorg Chem 32:1946–1950

    CAS  Google Scholar 

  54. Nesmeyanov AN, Perevalova EG, Struchkov YT, Antipin MY, Grandberg KI, Dyadchenko VP (1980) J Organomet Chem 201:343–349

    CAS  Google Scholar 

  55. Sherry BD, Toste FD (2004) J Am Chem Soc 126:15978–15979

    CAS  Google Scholar 

  56. Nieto-Oberhuber C, López S, Echavarren AM (2005) J Am Chem Soc 127:6178–6179

    CAS  Google Scholar 

  57. Herrero-Gómez E, Nieto-Oberhuber C, López S, Benet-Buchholz J, Echavarren AM (2006) Angew Chem Int Ed Engl 45:5455–5459

    Google Scholar 

  58. Partyka DV, Robilotto TJ, Zeller M, Hunter AD, Gray TG (2008) Organometallics 27:28–32

    CAS  Google Scholar 

  59. Nieto-Oberhuber C, López S, Muñoz MP, Jiménez-Núñez E, Buñuel E, Cárdenas DJ, Echavarren AM (2006) Chem Eur J 12:1694–1702

    CAS  Google Scholar 

  60. Jiménez-Núñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed Engl 45:5452–5455

    Google Scholar 

  61. Ferrer C, Echavarren AM (2006) Angew Chem Int Ed Engl 45:1105–1109

    CAS  Google Scholar 

  62. Ferrer C, Amijs CHM, Echavarren AM (2007) Chem Eur J 13:1358–1373

    CAS  Google Scholar 

  63. Mézailles N, Ricard L, Gagosz F (2005) Org Lett 7:4133–4136

    Google Scholar 

  64. Nolan SP (2011) Acc Chem Res 44:91–100

    CAS  Google Scholar 

  65. Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676

    Google Scholar 

  66. Alcarazo M, Stork T, Anoop A, Thiel W, Fürstner A (2010) Angew Chem Int Ed Engl 49:2542–2546

    CAS  Google Scholar 

  67. Amijs CHM, López-Carrillo V, Raducan M, Pérez-Galán P, Ferrer C, Echavarren AM (2008) J Org Chem 73:7721–7730

    CAS  Google Scholar 

  68. de Frémont P, Scott NM, Stevens ED, Nolan SP (2005) Organometallics 24:2411–2418

    Google Scholar 

  69. de Frémont P, Singh R, Stevens ED, Petersen JL, Nolan SP (2007) Organometallics 26:1376–1385

    Google Scholar 

  70. Deetlefs M, Raubenheimer HG, Esterhuysen MW (2002) Cat Today 72:29–41

    CAS  Google Scholar 

  71. Schneider SK, Herrmann WA, Herdtrweck EZ (2003) Anorg Allg Chem 629:2363–2370

    CAS  Google Scholar 

  72. Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, Lauterbach T, Rodríguez C, López S, Bour C, Rosellón A, Cárdenas DJ, Echavarren AM (2008) J Am Chem Soc 130:269–279

    CAS  Google Scholar 

  73. de Frémont P, Stevens ED, Fructos MR, Diaz-Requejo MM, Perez PJ, Nolan SP (2006) Chem Commun 2045–2047

    Google Scholar 

  74. de Frémont P, Marion N, Nolan SP (2009) J Organomet Chem 694:551–560

    Google Scholar 

  75. Li G, Zhang L (2007) Angew Chem Int Ed Engl 46:5156–5159

    CAS  Google Scholar 

  76. Ricard L, Gagosz F (2007) Organometallics 26:4704–4707

    CAS  Google Scholar 

  77. Gaillard S, Slawin AMZ, Nolan SP (2010) Chem Commun 46:2742–2744

    CAS  Google Scholar 

  78. Gaillard C, Bosson J, Ramón RS, Nun P, Slawin AMZ, Nolan SP (2010) Chem Eur J 46:13729–13740

    Google Scholar 

  79. Bartolomé C, Carrasco-Rando M, Coco S, Cordovilla C, Martín-Alvarez JM, Espinet P (2008) Inorg Chem 47:1616–1624

    Google Scholar 

  80. Bartolomé C, Ramiro Z, Pérez-Galán P, Bour C, Raducan M, Echavarren AM, Espinet P (2008) Inorg Chem 47:11391–11397

    Google Scholar 

  81. Bartolomé C, Ramiro Z, García-Cuadrado D, Pérez-Galán P, Raducan M, Bour C, Echavarren AM, Espinet P (2010) Organometallics 29:951–956

    Google Scholar 

  82. Bartolomé C, García-Cuadrado D, Ramiro Z, Espinet P (2010) Inorg Chem 49:9758–9764

    Google Scholar 

  83. Hashmi ASK, Lothschütz THC, Rominger F (2010) Adv Synth Catal 352:1315–1337

    CAS  Google Scholar 

  84. Frey GD, Dewhurst RD, Kousar S, Donnadieu B, Bertrand G (2008) J Organomet Chem 693:1674–1682

    CAS  Google Scholar 

  85. Zeng X, Soleilhavoup M, Bertrand G (2009) Org Lett 11:3166–3199

    CAS  Google Scholar 

  86. Zeng X, Frey GD, Kousar S, Bertrand G (2009) Chem Eur J 15:3056–3060

    CAS  Google Scholar 

  87. Kilpin KJ, Paul USD, Lee A-L, Crowley JD (2011) Chem Commun 47:328–330

    CAS  Google Scholar 

  88. Teller H, Flügge S, Goddard R, Fürstner A (2010) Angew Chem Int Ed Engl 49:1949–1953

    CAS  Google Scholar 

  89. Fortman GC, Nolan SP (2010) Organometallics 29:4579–4583

    CAS  Google Scholar 

  90. López S, Herrero-Gómez E, Pérez-Galán P, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed Engl 45:6029–6032

    Google Scholar 

  91. Hintermann L, Labonne A (2007) Synthesis 8:1121–1150

    Google Scholar 

  92. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079–3159

    CAS  Google Scholar 

  93. Li C-J (2005) Chem Rev 105:3095–3165

    CAS  Google Scholar 

  94. Li Z, Brouwer C, He C (2008) Chem Rev 108:3239–3265

    CAS  Google Scholar 

  95. Arcadi A (2008) Chem Rev 108:3266–3325

    CAS  Google Scholar 

  96. Muzart J (2008) Tetrahedron 64:5815–5849

    CAS  Google Scholar 

  97. Kutscheroff M (1881) Chem Ber 14:1540–1542

    Google Scholar 

  98. Harman WD, Dobson JC, Taube H (1989) J Am Chem Soc 111:3061–3062

    CAS  Google Scholar 

  99. Hiscox W, Jennings PW (1990) Organometallics 9:1997–1999

    CAS  Google Scholar 

  100. Tokunaga M, Wakatsuki Y (1998) Angew Chem Int Ed Engl 37:2867–2869

    CAS  Google Scholar 

  101. James BR, Rempel GL (1969) J Am Chem Soc 91:863–865

    CAS  Google Scholar 

  102. Tokunaga M, Wakatsuki Y (1999) Chem Abstr 131:352828. Jap Patent 11319576 A2

    Google Scholar 

  103. Meier IK, Marsella JA (1993) J Mol Catal 78:31–42

    CAS  Google Scholar 

  104. Norman ROC, Parr WJE, Thomas CB (1976) J Chem Soc Perkin Trans 1, 1983

    Google Scholar 

  105. Fukuda Y, Utimoto K (1991) J Org Chem 56:3729–3731

    CAS  Google Scholar 

  106. Teles JH, Schulz M (1997) Chem Abstr 127:121499. BASF AG, WO-A1 9721648

    Google Scholar 

  107. Bruce MI (1991) Chem Rev 91:197–257

    CAS  Google Scholar 

  108. Bruneau C, Dixneuf PH (1999) Acc Chem Res 32:311–323

    CAS  Google Scholar 

  109. Silvestre J, Hoffman R (1985) Helv Chim Acta 68:1461–1506

    CAS  Google Scholar 

  110. Wakatsuki Y, Koga N, Yamazaki H, Morokuma K (1994) J Am Chem Soc 116:8105–8111

    CAS  Google Scholar 

  111. de los Ríos I, Jiménez Tenorio M, Puerta MC, Valerga P (1997) J Am Chem Soc 119:6529–6538

    Google Scholar 

  112. Lein M, Rudolph M, Hashmi SK, Schwerdtfeger P (2010) Organometallics 29:2206–2210

    CAS  Google Scholar 

  113. Mizushima E, Cui D-M, Deb Nath DC, Hayashi T, Tanaka M (2006) Organic Syntheses 83:55

    Google Scholar 

  114. Deetlefts M, Raubenheimer HG, Esterhuysen MW (2002) Catalysis Today 72:29–41

    Google Scholar 

  115. Scheneider SK, Herrmann WA, Herdtweck EZ (2003) Anorg Allg Chem 629:2363–2370

    Google Scholar 

  116. Sanz S, Jones LA, Mohr F, Laguna M (2007) Organometallics 26:952–957

    CAS  Google Scholar 

  117. Leyva A, Corma A (2009) J Org Chem 74:2067–2074

    CAS  Google Scholar 

  118. Santos LL, Ruiz VR, Sabater MJ, Corma A (2008) Tetrahedron 64:7902–7909

    CAS  Google Scholar 

  119. Lee SI, Baed JY, Sim SH, Chung YK (2007) Synthesis 14:2107–2114

    Google Scholar 

  120. Marion N, Carlqvist P, Gealageas R, de Frémont P, Maseras F, Nolan SP (2007) Chem Eur J 13:6437–6451

    CAS  Google Scholar 

  121. Engel DA, Dudley GB (2006) Org Lett 8:4027–4029

    CAS  Google Scholar 

  122. Egi M, Yamaguchi Y, Fujiwara N, Akai S (2008) Org Lett 9:1867–1870

    Google Scholar 

  123. Marion N, Ramón RS, Nolan SP (2009) J Am Chem Soc 131:448–449

    CAS  Google Scholar 

  124. Kuram MR, Bhanuchandra M, Sahoo AK (2010) J Org Chem 75:2247–2258

    CAS  Google Scholar 

  125. Wessig P, Teubner J (2006) Synlett 10:1543–1546

    Google Scholar 

  126. Tian G-Q, Shi M (2007) Org Lett 9:4917–4920

    CAS  Google Scholar 

  127. Belting V, Krause N (2006) Org Lett 8:4489–4492

    CAS  Google Scholar 

  128. Kirsch SF, Binder JT, Liébert C, Menz H (2006) Angew Chem Int Ed Engl 45:5878–5880

    CAS  Google Scholar 

  129. Harkat H, Weibel J-M, Pale P (2007) Tetrahedron Lett 48:1439–1442

    CAS  Google Scholar 

  130. Liu B, De Brabander JK (2006) Org Lett 8:4907–4910

    CAS  Google Scholar 

  131. Volchkov I, Sharma K, Cho EJ, Lee D (2011) Chem Asian J 6:1961–1966

    Google Scholar 

  132. Barluenga J, Calleja J, Mendoza A, Rodríguez F, Fañanás FJ (2010) Chem Eur J 16:7110–7112

    CAS  Google Scholar 

  133. Barluenga J, Fernández A, Diéguez A, Rodríguez F, Fañanás FJ (2009) Chem Eur J 15:11660–116602

    CAS  Google Scholar 

  134. Dai L-Z, Qi M-J, Shi Y-L, Liu X-G, Shi M (2007) Org Lett 9:3191–3194

    CAS  Google Scholar 

  135. Balamurugan R, Kothapalli RB, Thota GK (2011) Eur J Org Chem 1557–1569

    Google Scholar 

  136. Jung HH, Floreancig PE (2006) Org Lett 8:1949–1951

    CAS  Google Scholar 

  137. Jung HH, Floreancig PE (2007) J Org Chem 72:7359–7366

    CAS  Google Scholar 

  138. Dubé P, Toste FD (2006) J Am Chem Soc 128:12062–12063

    Google Scholar 

  139. Renault J, Qian Z, Uriac P, Gouault N (2011) Tetrahedron Lett 52:2476–2479

    CAS  Google Scholar 

  140. Ghosh N, Nayak S, Sahoo AK (2011) J Org Chem 76:500–511

    CAS  Google Scholar 

  141. Robles-Machín R, Adrio J, Carretero JC (2006) J Org Chem 71:5023–5026

    Google Scholar 

  142. Das A, Chang H-K, Yang C-H, Liu R-S (2008) Org Lett 10:4061–4064

    CAS  Google Scholar 

  143. Sperger C, Fiksdahl A (2009) Org Lett 11:2449–2452

    CAS  Google Scholar 

  144. Sperger C, Strand LHS, Fiksdahl A (2010) Tetrahedron 66:7749–7754

    CAS  Google Scholar 

  145. Wilckens K, Uhlemann M, Czekelius C (2009) Chem Eur J 15:13323–13326

    CAS  Google Scholar 

  146. Genin E, Toullec PY, Antoniotti S, Brancour C, Genêt J-P, Michelet V (2006) J Am Chem Soc 128:3112–3113

    CAS  Google Scholar 

  147. Harkat H, Weibel J-M, Pale P (2006) Tetrahedron Lett 47:6273–6276

    CAS  Google Scholar 

  148. Kang J-E, Shin S (2006) Synlett 10:717–720

    Google Scholar 

  149. Wang W, Xu B, Hammond GB (2009) J Org Chem 74:1640–1643

    CAS  Google Scholar 

  150. Körner C, Starkov P, Sheppard TD (2010) J Am Chem Soc 132:5968–5969

    Google Scholar 

  151. Xu B, Wang W, Liu L-P, Han J, Jin Z, Hammond GB (2011) J Organomet Chem 696:269–276

    CAS  Google Scholar 

  152. Zhang G, Cui L, Wang Y, Zhang L (2010) J Am Chem Soc 132:1474–1475

    CAS  Google Scholar 

  153. Brenzovich WE, Brazeau J-F, Toste FD (2010) Org Lett 12:4728–4731

    CAS  Google Scholar 

  154. Melhado AD, Brenzovich WE, Lackner AD, Toste FD (2010) J Am Chem Soc 132:8885–8887

    CAS  Google Scholar 

  155. Kinjo R, Donnadieu B, Bertrand G (2011) Angew Chem Int Ed Engl 50:5560–5563

    CAS  Google Scholar 

  156. Leyva-Perez A, Cabrero-Antonio JR, Cantin A, Corma A (2010) J Org Chem 75:7769–7780

    CAS  Google Scholar 

  157. Lavallo V, Frey GD, Donnadieu B, Soleihavoup M, Bertrand G (2008) Angew Chem Int Ed Engl 47:5224–5228

    CAS  Google Scholar 

  158. Corma A, Concepción P, Domínguez I, Forne V, Sabter MJ (2007) J Catal 251:39–47

    CAS  Google Scholar 

  159. Duan H, Sengupta S, Petersen JL, Akhmedov NG, Shi X (2009) J Am Chem Soc 131:121000–121002

    Google Scholar 

  160. Corma A, González-Arellano C, Iglesias M, Sánchez F (2010) Applied Catal A Gen 375:49–54

    CAS  Google Scholar 

  161. Díez-Golzález S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676

    Google Scholar 

  162. Norman ROC, Parr WJE, Thomas B (1976) J C S Perkin Trans 1:811–817

    Google Scholar 

  163. Lethbridge A, Norman ROC, Thomas B(1974) J Chem Soc Perkin I 1929–1938

    Google Scholar 

  164. Lethbridge A, Norman ROC, Thomas B, Parr WJE (1975) J Chem Soc Perkin I 231–241

    Google Scholar 

  165. Yang C-G, He C (2005) J Am Chem Soc 127:6966–6967

    CAS  Google Scholar 

  166. Hirai T, Hamasaki A, Nakamura A, Tokunaga M (2009) Org Lett 11:5510–5513

    CAS  Google Scholar 

  167. Li Z, Zhang J, Brouwer C, Yang C-G, Reich NW, He C (2006) Org Lett 8:4175–4178

    CAS  Google Scholar 

  168. Rosenfeld DC, Secar S, Takemiya A, Utsunomiya M, Hartwig JF (2006) Org Lett 8:4179–4182

    CAS  Google Scholar 

  169. Reich NW, Yang C-G, Shi Z, He C (2006) Synlett 8:1278–1280

    Google Scholar 

  170. Nguyen R-V, Yao X, Li C-J (2006) Org Lett 8:2397–2399

    CAS  Google Scholar 

  171. Hadfield MS, Bauer JT, Glen PE, Lee A-L (2010) Org Biomol Chem 8:4090–4095

    CAS  Google Scholar 

  172. Zang X, Corma A (2007) Chem Commun 30803082

    Google Scholar 

  173. Zang X, Corma A (2008) Dalton Trans 397–403

    Google Scholar 

  174. Corberán R, Marrot S, Dellus N, Merceron-Saffon N, Kato T, Peris E, Baceiredo A (2009) Organometallics 28:326–330

    Google Scholar 

  175. Bandini M, Monari M, Romaniello A, Tragni M (2010) Chem Eur J 16:14272–14277

    CAS  Google Scholar 

  176. Aponick A, Biannic B (2011) Org Lett 6:1330–1333

    Google Scholar 

  177. Hoffmann-Röder A, Krause N (2001) Org Lett 3:2537–2538

    Google Scholar 

  178. Hashmi ASK, Scjwarz L, Choi JH, Frost TM (2000) Angew Chem Int Ed Engl 39:2285–2288

    CAS  Google Scholar 

  179. Marshall JA, Wang XJ (1991) J Org Chem 56:4913–4918

    CAS  Google Scholar 

  180. Hashmi ASK, Blanco MC, Fischer D, Bats JW (2006) Eur J Org Chem 1387–1389

    Google Scholar 

  181. Hyland CJT, Hegedus LS (2006) J Org Chem 71:8658–8660

    CAS  Google Scholar 

  182. Minkler SRK, Lipshutz BH, Krause N, (2011) Angew Chem Int Ed 50:7820–7823

    Google Scholar 

  183. Gockel B, Krause N (2006) Org Lett 8:4485–4488

    CAS  Google Scholar 

  184. Deutsch C, Gockel B, Hoffmann-Röder A, Krause N (2007) Synlett 11:1790–1794

    Google Scholar 

  185. Asikainen M, Krause N (2009) Adv Synth Catal 351:2308–2309

    Google Scholar 

  186. Volz F, Krause N (2007) Org Biomol Chem 5:1519–1521

    CAS  Google Scholar 

  187. Erdsack J, Krause N (2007) Synthesis 23:3741–3750

    Google Scholar 

  188. Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA (2006) J Am Chem Soc 128:9066–9073

    CAS  Google Scholar 

  189. Zhang Z, Widenhoefer RA (2007) Angew Chem Int Ed Engl 46:283–285

    CAS  Google Scholar 

  190. Hamilton GL, Kang EJ, Mba M, Toste FD (2007) Science 317:496–499

    CAS  Google Scholar 

  191. Wang ZJ, Brown CJ, Bergman RG, Raymond KN, Toste FD (2011) J Am Chem Soc 133:7358–7360

    CAS  Google Scholar 

  192. Dudnik AS, Gevorgyan V (2007) Angew Chem Int Ed Engl 46:5195–5197

    CAS  Google Scholar 

  193. Zhou C-U, Chan PWH, Che C-M (2006) Org Lett 8:325–328

    CAS  Google Scholar 

  194. Sromek AW, Rubina M, Gevorgyan V (2005) J Am Chem Soc 127:10500–10501

    CAS  Google Scholar 

  195. Buzas AK, Istrate FM, Gagosz F (2007) Org Lett 9:985–988

    CAS  Google Scholar 

  196. Zhang Z, Widenhoefer RA (2008) Org Lett 10:2079–2081

    CAS  Google Scholar 

  197. Zhang Z, Lee SD, Fisher AS, Widenhoefer RA (2009) Tetrahedron 65:1794–1798

    CAS  Google Scholar 

  198. Nishina N, Yamamoto Y (2008) Tetrahedron 65:1799–1808

    Google Scholar 

  199. Cui D-M, Yu K-R, Zang C (2009) Synlett 7:1103–1106

    Google Scholar 

  200. Cui D-M, Zheng Z-L, Zang C (2009) J Org Chem 74:1426–1427

    CAS  Google Scholar 

  201. Muñoz MP, Adrio J, Carretero JC, Echavarren AM (2005) Organometallics 24:1293–1300

    Google Scholar 

  202. Buzas AK, Istrate FM, Gagosz F (2007) Angew Chem Int Ed Engl 46:1141–1144

    CAS  Google Scholar 

  203. Luzung MR, Markham JP, Toste FD (2004) J Am Chem Soc 126:10858–10859

    CAS  Google Scholar 

  204. Zhang L, Kozmin SA (2005) J Am Chem Soc 127:6962–6963

    CAS  Google Scholar 

  205. Buzas A, Istrate F, Le Goff XF, Odabachian Y, Gagosz F (2009) J Organomet Chem 694:515–519

    CAS  Google Scholar 

  206. Lee Y, Lim C, Kim S, Shin S (2010) Bull Korean Chem Soc 31:670–677

    CAS  Google Scholar 

  207. Toullec PY, Blarre T, Michelet V (2009) Org Lett 11:2888–2891

    CAS  Google Scholar 

  208. Imagawa H, Iyenaga T, Nishizawa M (2005) Org Lett 7:451–453

    CAS  Google Scholar 

  209. Sherry BD, Maus L, Laforteza BN (2006) J Am Chem Soc 128:8132–8133

    CAS  Google Scholar 

  210. Mauleón P, Krinsky JL, Toste FD (2009) J Am Chem Soc 131:4513–4520

    Google Scholar 

  211. Suhre MH, Reif M, Kirsch SF (2005) Org Lett 7:3925–3927

    CAS  Google Scholar 

  212. Wei H, Wang Y, Yue B, Xu P-F (2010) Adv Synth Catal 352:2450–2454

    CAS  Google Scholar 

  213. Nevado C, Echavarren AM (2004) Tetrahedron 60:9735–9744

    CAS  Google Scholar 

  214. Park S, Lee D (2006) J Am Chem Soc 128:10664–10665

    CAS  Google Scholar 

  215. Horino Y, Luzung MR, Toste FD (2006) J Am Chem Soc 128:11364–11365

    CAS  Google Scholar 

  216. Méndez M, Muñoz MP, Nevado C, Cárdenas DJ, Echavarren AM (2001) J Am Chem Soc 123:10511–10520

    Google Scholar 

  217. Méndez M, Muñoz MP, Echavarren AM (2000) J Am Chem Soc 122:11549–11550

    Google Scholar 

  218. Nevado C, Cárdenas DJ, Echavarren AM (2003) Chem Eur J 9:2627–2635

    CAS  Google Scholar 

  219. Muñoz MP, Méndez M, Nevado C, Cárdenas DJ, Echavarren AM (2003) Synthesis 2898–2902

    Google Scholar 

  220. Nevado C, Charruault L, Michelet V, Nieto-Oberhuber C, Muñoz MP, Méndez M, Rager MN, Genêt J-P, Echavarren AM (2003) Eur J Org Chem 706–713

    Google Scholar 

  221. Michelet V, Charruault L, Gladiali S, Genêt J-P (2006) Pure Appl Chem 78:397–407

    CAS  Google Scholar 

  222. Charrualt L, Michelet V, Taras R, Gladiali S, Genêt J-P (2004) Chem Commun 850–851

    Google Scholar 

  223. Galland J-C, Savignac M, Genêt JP (1997) Tetrahedron Lett 38:8695–8698

    CAS  Google Scholar 

  224. Galland J-C, Dias S, Savignac M, Genêt JP (2001) Tetrahedron 57:5137–5148

    CAS  Google Scholar 

  225. Charruault L, Michelet V, Genêt JP (2002) Tetrahedron Lett 43:4757–4760

    CAS  Google Scholar 

  226. Faller JW, Fontaine PP (2006) J Organomet Chem 691:1912–1918

    CAS  Google Scholar 

  227. Nieto-Oberhuber C, Muñoz MP, López S, Jiménez-Nuñez E, Nevado C, Herrero-Gómez E, Raducan M, Echavarren AM (2005) Chem Eur J 127:6178–6179

    CAS  Google Scholar 

  228. Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, Lauterbach T, Rodríguez C, López S, Bour C, Echavarren AM (2008) J Am Chem Soc 130:269–279

    CAS  Google Scholar 

  229. Genin E, Leseurre L, Toullec PY, Genêt J-P, Michelet V (2007) Synlett 11:1780–1784

    Google Scholar 

  230. Chao C-M, Genin E, Toullec PY, Genêt J-P, Michelet V (2009) J Organomet Chem 694:538–545

    CAS  Google Scholar 

  231. Bartolomé C, Ramiro Z, Gracía-Cuadro D, Pérez-Galán P, Raducan M, Bour C, Echavarren AM, Espinet P (2010) Organometallics 29:951–956

    Google Scholar 

  232. Pradal A, Chao C-M, Vitale MR, Toullec PY, Michelet V (2011) Tetrahedron 67:4371–4377

    CAS  Google Scholar 

  233. Fürstner A, Morency L (2008) Angew Chem Int Ed Engl 47:5030–5033

    Google Scholar 

  234. Nieto-Oberhuber C, López S, Jiménez-Nuñez E, Echavarren AM (2006) Chem Eur J 12:5916–5923

    CAS  Google Scholar 

  235. Bajracharya GB, Nakamura I, Yamamoto Y (2005) J Org Chem 70:892–897

    CAS  Google Scholar 

  236. Matsumoto Y, Selim KB, Nakanishi H, Yamada K, Yamamoto Y, Tomioka K (2010) Tetrahedron Lett 51:404–406

    CAS  Google Scholar 

  237. Luzung MR, Mauleón P, Toste FD (2007) J Am Chem Soc 129:12402–12403

    CAS  Google Scholar 

  238. Chatai N, Morimoto T, Muto T, Murai S (1994) J Am Chem Soc 116:6049–6050

    Google Scholar 

  239. Chatani N, Rurukawa N, Sakurai H, Murai S (1996) Organometallics 15:901–903

    CAS  Google Scholar 

  240. Miyanohana Y, Inoue H, Chatani N (2004) J Org Chem 69:8541–8543

    CAS  Google Scholar 

  241. Oh CH, Bang SY, Rgim CY (2003) Bull Korean Chem Soc 24:887–888

    CAS  Google Scholar 

  242. Chatani N, Inoue H, Morimoto T, Muto T, Murai S (2001) J Org Chem 66:4433–4436

    CAS  Google Scholar 

  243. Chatani N, Inoue H, Kotsuma T, Murai S (2002) J Am Chem Soc 124:10294–10295

    CAS  Google Scholar 

  244. Kim SM, Lee SI, Cheng YK (2006) Org Lett 8:5425–5427

    CAS  Google Scholar 

  245. Simmons EM, Sarpong R (2006) Org Lett 8:2883–2886

    CAS  Google Scholar 

  246. Miyanohana Y, Chatani N (2006) Org Lett 8:2155–2158

    CAS  Google Scholar 

  247. Oi S, Tsukamoto I, Miyano S, Inoue Y (2001) Organometallics 20:3704–3709

    CAS  Google Scholar 

  248. Ochida A, Ito H, Sawamura M (2006) J Am Chem Soc 128:16486–16487

    CAS  Google Scholar 

  249. Nishizawa M, Yadav VK, Skwarczynski M, Takao H, Imagawa H, Sugihara T (2003) Org Lett 5:1609–1611

    CAS  Google Scholar 

  250. Cabello N, Rodríguez C, Echavarren AM (2007) Synlett 11:1753–1758

    Google Scholar 

  251. Pérez-Galán P, Delpont N, Herrero-Gómez E, Maseras F, Echavarren AM (2010) Chem Eur J 16:5324–5332

    Google Scholar 

Download references

Acknowledgments

We thank the MICINN (CTQ2010-16088/BQU, Consolider Ingenio 2010 Grant CSD2006-0003, and FPU predoctoral fellowship to N.H.), the AGAUR (2009 SGR 47), and the ICIQ Foundation for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Antonio M. Echavarren .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Huguet, N., Echavarren, A.M. (2011). Gold-Catalyzed O–H Bond Addition to Unsaturated Organic Molecules. In: Ananikov, V., Tanaka, M. (eds) Hydrofunctionalization. Topics in Organometallic Chemistry, vol 43. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2011_21

Download citation

Publish with us

Policies and ethics