Gold-catalyzed reactions of C-H bonds

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 4917-4938

  Skouta, Rachid ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE DERIVATIVE; AMINE; GOLD;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 42749087843     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.083     Document Type: Review

References (200)

1. There are numerous reports; for examples, see:
2. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
3. Zeni G., and Larock R.C. Chem. Rev. 104 (2004) 2285
4. Li C.-J. Acc. Chem. Res. 35 (2002) 533
5. Ritleng V., Sirlin C., and Pfeffer M. Chem. Rev. 102 (2002) 1731
6. Jia C., Kitamura T., and Fujiwara Y. Acc. Chem. Res. 34 (2001) 633
7. Guari Y., Sabo-Etienne S., and Chaudret B. Eur. J. Inorg. Chem. 71 (1999) 47
8. For representative reviews, see:
9. Hashmi A.S.K. Angew. Chem., Int. Ed. 44 (2005) 6990
10. Höffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387
11. Ma S., Yu S., and Gu Z. Angew. Chem., Int. Ed. 44 (2005) 2
12. Hashmi A.S.K. Gold Bull. 37 (2004) 51
13. Arcadi A., and Di Giuseppe S. Curr. Org. Chem. 8 (2004) 795
14. Bianchi G., and Arcadi A. Targets Heterocycl. Syst. 8 (2004) 82
15. Hashmi A.S.K. Gold Bull. 36 (2003) 3
16. Dyker G. Angew. Chem., Int. Ed. 39 (2000) 4237
17. Reviews:
18. Thompson D. Gold Bull. 31 (1998) 111
19. Thompson D. Gold Bull. 32 (1999) 12
20. Bond G.C. Catal. Today 72 (2002) 5
21. Georgy M., Boucard V., and Campagne J.-M. J. Am. Chem. Soc. 127 (2005) 14180
22. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 127 (2005) 6962
23. Gagosz F. Org. Lett. 7 (2005) 4129
24. Nieto-Oberhuber C., López S., and Echavarren A.M. J. Am. Chem. Soc. 127 (2005) 6178
25. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 11806
26. Luzung M.R., Markham J.P., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 10858
27. Sherry B.D., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 15978
28. Mamane V., Gress T., Krause H., and Fürstner A. J. Am. Chem. Soc. 126 (2004) 8654
29. Nieto-Oberhuber C., Muñoz M.P., Bunuel E., Nevado C., Cardenas D.J., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 2402
30. Nevado C., Cardenas D.J., and Echavarren A.M. Chem.-Eur. J. 9 (2003) 2627
31. Hashmi A.S.K., Frost T.M., and Bats J.W. J. Am. Chem. Soc. 122 (2000) 11553
32. Reich N.W., Yang C.-G., Shi Z., and He C. Synlett (2006) 1278
33. Sherry B.D., Maus L., Laforteza B.N., and Toste F.D. J. Am. Chem. Soc. 128 (2006) 8132
34. Nieto-Oberhuber C., Muñoz M.P., Lópezl S., Jimenez-Nunez E., Nevado C., Herrero-Gomez E., Raducan M., and Echavarren A.M. Chem.-Eur. J. 12 (2006) 1677
35. Marion N., de Frémont P., Lemière G., Stevens E.D., Fensterbank L., Malacria M., and Nolan S.P. Chem. Commun. (2006) 2048
36. Poli G., Giambastiani G., and Heumann A. Tetrahedron 56 (2000) 5959
37. Heumann A., and Reglier M. Tetrahedron 52 (1996) 9289
38. Meijere A.D., and Brase S. J. Organomet. Chem. 576 (1999) 88
39. Tietze L.F. Chem. Rev. 96 (1996) 115
40. Balme G., Bossharth E., and Monteiro N. Eur. J. Org. Chem. (2003) 4101
41. Ramon D.J., and Yus M. Angew. Chem., Int. Ed. 44 (2005) 1602
42. Ito Y., Sawamura M., and Hayashi T. J. Am. Chem. Soc. 108 (1986) 6405
43. Sawamura M., Ito Y., and Hayashi T. Tetrahedron Lett. 30 (1989) 2247
44. Sawamura M., Nakayama Y., Kato T., and Ito Y. J. Org. Chem. 60 (1995) 1727
45. Ito H., Yajima T., Tateiwa J.-I., and Hosomi A. Chem. Commun. (2000) 981
46. Fukuda Y., and Utimoto K. J. Org. Chem. 56 (1991) 3729
47. Fukuda Y., and Utimoto K. Bull. Chem. Soc. Jpn. 64 (1991) 2013
48. Teles J.H., Brode S., and Chabanas M. Angew. Chem., Int. Ed. 37 (1998) 1415
49. See Ref. 4k.
50. Hashmi A.S.K., Schwarz L., Choi J.H., and Frost T.M. Angew. Chem., Int. Ed. 39 (2000) 2285
51. See Ref. 2g.
52. Hayashi T., Sawamura M., and Ito Y. Tetrahedron 48 (1992) 1999
53. Dyker G., Hildebrandt D., Liu J., and Merz K. Angew. Chem., Int. Ed. 42 (2003) 4399
54. Herrerias C.I., Yao X., Li Z., and Li C.-J. Chem. Rev. 107 (2007) 2546
55. Chen L., and Li C.-J. Chem. Soc. Rev. 35 (2006) 68
56. Li C.-J. Chem. Rev. 105 (2005) 3095
57. See Ref. 1c.
58. Lindstrom U.M. Chem. Rev. 102 (2002) 2751
59. Li C.-J. Chem. Rev. 93 (1993) 2023
60. Skouta R., Varma R.S., and Li C.-J. Green Chem. 7 (2005) 571
61. Li H.-J., Zhao J.-L., Chen Y.-J., Li L., Wang D., and Li C.-J. Green Chem. 7 (2005) 61
62. Yao X., and Li C.-J. Org. Lett. 8 (2006) 1953
63. Maruse N., and Goto M. J. Antibiot. 51 (1998) 545
64. Wang W., Breining T., Li T., Milbum R., and Attardo G. Tetrahedron Lett. 39 (1998) 2459 and the references therein
65. Another possible mechanism might involve the formation of a benzopyrylium cation in the benzannulation of o-alkynyl(oxo)-benzenes with alkynes. For other recent related examples, see:. Kusama H., Miyashita Y., Takaya J., and Iwasawa N. Org. Lett. 8 (2006) 289 However, in all these cases, high-valent metals and/or non-coordinating anions are required
66. 3P gives the best results.
67. Cozzi P.G., Hilgraf N., and Zimmermann N. Eur. J. Org. Chem. (2004) 4905
68. Prajapati D., Laskar D.D., Gogoi B.J., and Devi G. Tetrahedron Lett. 44 (2003) 6755
69. Wei C., and Li C.-J. J. Am. Chem. Soc. 125 (2003) 9584
70. Kabalka G.W., Wang L., and Pagni R.M. Synlett (2001) 676
71. Shi L., Tu Y.Q., Wang M., Zhang F.M., and Fan C.A. Org. Lett. 6 (2004) 1001
72. Gommermann N., Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 5763
73. Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 41 (2002) 2535
74. Syeda H.Z.S., Halder R., Karla S.S., Das J., and Iqbal J. Tetrahedron Lett. 43 (2002) 6485
75. Choudary B.M., Sridhar Ch., Kantam M.L., and Sreedhar B. Tetrahedron Lett. 45 (2004) 7319
76. Wei C.M., and Li C.-J. Chem. Commun. (2002) 268
77. Fischer C., and Carreira E.M. Org. Lett. 3 (2001) 4319
78. Satoshi S., Takashi K., and Ishii Y. Angew. Chem., Int. Ed. 40 (2001) 2534
79. Li Z.G., Wei C.M., Chen L., Varma R.S., and Li C.-J. Tetrahedron Lett. 45 (2004) 2443
80. Wei C.M., Li Z.G., and Li C.-J. Org. Lett. 5 (2003) 4473 and references cited therein
81. For synthesizing alkynyl gold complexes, see:. Vicente J., Chicote M.T., and Abrisqueta M.D. J. Chem. Soc., Dalton Trans. (1995) 497
82. Huang B., Yao X., and Li C.-J. Adv. Synth. Catal. 348 (2006) 1528
83. Lo V.K.-Y., Liu Y., Wong M.-K., and Che C.-M. Org. Lett. 8 (2006) 1529
84. Barnholtz S.L., Lydon J.D., Huang G., Venkatesh M., Barnes C.L., Ketring A.R., and Jurisson S.S. Inorg. Chem. 40 (2001) 972
85. Yan B., and Liu Y. Org. Lett. 9 (2007) 4323
86. Kantam M.L., Prakash B.V., Reddy C.R.V., and Sreedhar B. Synlett (2005) 2329
87. Miyata S. Clays Clay Miner. 23 (1975) 369
88. Kidwai M., Bansal V., Kumar A., and Mozumdar S. Green Chem. 9 (2007) 742
89. Zhang J., Wei C., and Li C.-J. Tetrahedron Lett. 43 (2002) 5731
90. Black A.D., and Arndtsen B.A. Org. Lett. 6 (2004) 1107
91. Fischer C., and Carreira E.M. Org. Lett. 6 (2004) 1497
92. Wei C., and Li C.-J. Lett. Org. Chem. 2 (2005) 410
93. Trost B.M. Science 254 (1991) 1471
94. Trost B.M. Angew. Chem., Int. Ed. Engl. 34 (1995) 259
95. Sheldon R.A. Pure Appl. Chem. 72 (2000) 1233
96. Kharasch M.S., and Isbell H.S. J. Am. Chem. Soc. 53 (1931) 3053
97. Liddle K.S., and Parkin C. J. Chem. Soc., Chem. Commun. (1972) 26
98. de Graaf P.W.J., Boersma J., and van der Kerk G.J.M. J. Organomet. Chem. 105 (1976) 399
99. Fuchita Y., Utsunomiya Y., and Yasutake M. J. Chem. Soc., Dalton Trans. (2001) 2330
100. Reetz M.T., and Sommer K. Eur. J. Org. Chem. (2003) 3485
101. Shi Z., and He C. J. Org. Chem. 69 (2004) 3669
102. Nevado C., and Echavarren A.M. Chem.-Eur. J. 11 (2005) 3155
103. Ferrer C., and Echavarren A.M. Angew. Chem., Int. Ed. 45 (2006) 1105
104. Ferrer C., Amijs C.H.M., and Echavarren A.M. Chem.-Eur. J. 13 (2007) 1358
105. Herrero-Gomez E., Nieto-Oberhuber C., López S., Benet-Buchholz J., and Echavarren A.M. Angew. Chem., Int. Ed. 45 (2006) 5455
106. Nieto-Oberhuber C., López S., MuIoz M.P., Cárdenas D.J., BuIuel E., Nevado C., and Echavarren A.M. Angew. Chem., Int. Ed. 44 (2005) 6146
107. See Ref. 4d.
108. Marion N., Díez-González S., De-Frémont P., Noble A.R., and Nolan S.P. Angew. Chem., Int. Ed. 45 (2006) 3647
109. For the synthesis of a series of (NHC)AuCl complexes, see:. De Fremont P., Scott N.M.E., Stevens D., and Nolan S.P. Organometallics 24 (2005) 2411
110. Peng L., Zhang X., Zhang S., and Wang J. J. Org. Chem. 72 (2007) 1192
111. Arcadi A., Bianchi G., Chiarini M., D'Anniballe G., and Marinelli F. Synlett (2004) 944
112. Arcadi A., Alfonso M., Bianchi G., D'Anniballe G., and Marinelli F. Adv. Synth. Catal. 348 (2006) 331
113. Alfonso M., Arcadi A., Bianchi G., Marinelli F., and Nardini A. Eur. J. Org. Chem. (2006) 2393
114. Itahara T., Kawasaki K., and Ouseto F. Synthesis (1984) 236
115. Itahara T., Ikeda M., and Sakakibara T. J. Chem. Soc., Perkin Trans. 1 (1983) 1361
116. Baker R.T., Nguyen P., Marder T.B., and Westcott S.A. Angew. Chem., Int. Ed. Engl. 34 (1995) 1336
117. Shi Z., and He C. J. Organomet. Chem. 690 (2005) 5049
118. Bielsa R., Larrea A., Navarro R., Soler T., and Urriolabeitia E.P. Eur. J. Inorg. Chem. (2005) 1724
119. Aguilar D., Contel M., Navarro R., and Urriolabeitia E.P. Organometallics 26 (2007) 4604
120. For other cycloaurated derivatives containing C, N-pincer ligands see:
121. Bonnardel P.A., Parish R.V., and Pritchard R.G. J. Chem. Soc., Dalton Trans. (1996) 3185
122. Constable E.C., and Leese T.A. J. Organomet. Chem. 363 (1989) 419
123. Vicente J., Chicote M.T., and Bermúdez M.D. J. Organomet. Chem. 268 (1984) 191
124. Watanabe T., Oishi S., Fujii N., and Ohno H. Org. Lett. 9 (2007) 4821
125. Luo Y., and Li C.-J. Chem. Commun. (2004) 1930
126. Youn S.W. J. Org. Chem. 71 (2006) 2521
127. Shi Z., and He C. J. Am. Chem. Soc. 126 (2004) 5964
128. Shi Z., and He C. J. Am. Chem. Soc. 126 (2004) 13596
129. Kennedy-Smith J.J., Staben S.T., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 4526
130. Yao X., and Li C.-J. J. Am. Chem. Soc. 126 (2004) 6884
131. Nguyen R.V., and Li C.-J. Org. Lett. 7 (2005) 673
132. Zhou C.-Y., and Che C.-M. J. Am. Chem. Soc. 129 (2007) 5828
133. Harbone J.B., and Williams C.A. Nat. Prod. Rep. 18 (2001) 310
134. Achutz B.A., Wright A.D., Rali T., and Sticher O. Phytochemistry 40 (1995) 1273
135. Lin Y.M., Zhou Y., Flavin M.T., and Zhou L.M. Bioorg. Med. Chem. 10 (2002) 2795
136. Park M.-S., and Lee J.I. Bull. Korean Chem. Soc. 25 (2004) 1269 and Refs. 4-11 therein
137. Skouta R., and Li C.-J. Angew. Chem., Int. Ed. 46 (2007) 1117
138. Hildebrandt D., and Dyker G. J. Org. Chem. 71 (2006) 6728
139. Murray III H.H., Fackler Jr. J.P., and Tocher D.A. J. Chem. Soc., Chem. Commun. (1985) 1278 and Ref. 1a cited therein
140. White-Morris R.L., Olmstead M.M., Jiang F., Tinti D.S., and Balch A.L. J. Am. Chem. Soc. 124 (2002) 2327
141. Schneider S.K., Herrmann W.A., and Herdtweck E. Z. Anorg. Allg. Chem. 629 (2003) 2363
142. Fructos M.R., Belderrain T.R., Frémont P.-D., Scott N.M., Nolan S.P., Díaz-Requejo M.M., and Pérez P.J. Angew. Chem., Int. Ed. 44 (2005) 5284
143. Hashmi A.S.K., Schäfer S., Wölfle M., Gil C.D., Fischer P., Laguna A., Blanco M.C., and Gimeno M.C. Angew. Chem., Int. Ed. 46 (2007) 6184
144. Skouta R., and Li C.-J. Tetrahedron Lett. 48 (2007) 8343
145. Skouta R., and Li C.-J. Synlett (2007) 1759
146. Liu X.-Y., Ding P., Huang J.-S., and Che C.-M. Org. Lett. 9 (2007) 2645
147. Luo Y., Li Z., and Li C.-J. Org. Lett. 7 (2005) 2675
148. Toullec P.Y., Genin E., Leseurre L., Genet J.P., and Michelet V. Angew. Chem., Int. Ed. 45 (2006) 7427
149. Genin E., Leseurre L., Toullec P.Y., Genet J.-P., and Michelet V. Synlett (2007) 1780
150. Amijs C.H.M., Ferrer C., and Echavarren A.M. Chem. Commun. (2007) 698
151. See Ref. 9b.
152. Nguyen R.-V., Yao X., and Li C.-J. Org. Lett. 8 (2006) 2397
153. Arndtsen B.A., Bergman R.G., Mobley T.A., and Peterson T.H. Acc. Chem. Res. 28 (1995) 154
154. Shilov A.E., and Shul'pin G.B. Chem. Rev. 97 (1997) 2879
155. Crabtree R.H. J. Chem. Soc., Dalton Trans. 17 (2001) 2437
156. Jones W.D. Science 287 (2000) 1942
157. Periana R.A., Taube D.J., Evitt E.R., Loffler D.G., Wentrcek P.R., Voss G., and Masuda T. Science 259 (1993) 340
158. Periana R.A., Mironov O., Taube D., Bhalla G., and Jones C.J. Science 301 (2003) 814
159. Sen A. Acc. Chem. Res. 31 (1998) 550
160. Xu K.X.J., Periana R.A., and Goddard III W.A. Organometallics 22 (2003) 2057
161. Labinger J.A., and Bercaw J.E. Nature 417 (2002) 507
162. Lin M., Shen C., Garcia-Zayas E.A., and Sen A. J. Am. Chem. Soc. 123 (2001) 1000
163. Periana R.A., Taube D.J., Gamble S., Taube H., Satoh T., and Fuji H. Science 280 (1998) 560
164. Stahl S., Labinger J.A., and Bercaw J.E. Angew. Chem., Int. Ed. 37 (1998) 2180
165. See Ref. 77b.
166. Jones C.J., Taube D., Ziatdinov V.R., Periana R.A., Nielsen R.J., Oxgaard J., and Goddard III W.A. Angew. Chem., Int. Ed. 43 (2004) 4626
167. De Vos D.E., and Sels B.F. Angew. Chem., Int. Ed. 44 (2005) 30
168. Zhao R., Ji D., Lv G., Qian G., Yan L., Wang X., and Suo J. Chem. Commun. (2004) 904
169. Xu Y.-J., Landon P., Enache D., Carley A.F., Roberts M.W., and Hutchings G.J. Catal. Lett. 101 (2005) 175
170. Shul'pin G.B., Shilov A.E., and Süss-Fink G. Tetrahedron Lett. 42 (2001) 7253
171. Shul'pin G.B., Guerreiro M.C., and Schuchardt U. Tetrahedron 52 (1996) 13051
172. Guan B., Xing D., Cai G., Wan X., Yu N., Fang Z., Yang L., and Shi Z. J. Am. Chem. Soc. 127 (2005) 18004
173. Choudhary V.R., Dumbre B.S., Jana P., Uphade B.S., and Narkhede V.S. J. Mol. Catal. A: Chem. 215 (2004) 129
174. Choudhary V.R., Dhar A., Jana P., Jha R., and Uphade B.S. Green Chem. 7 (2005) 768
175. Choudhary V.R., Jha R., and Jana P. Green Chem. 9 (2007) 267
176. Zheng N., and Stucky G.D. Chem. Commun. (2007) 3862
177. Enache D.I., Edwards J.K., Landon P., Solsona-Espriu B., Carley A.F., Herzing A.A., Watanabe M.I., Kiely C.J., Knight D.W., and Hutchings G.J. Science 311 (2006) 362
178. Li G., Enache D.I., Edwards J., Carley A.F., Knight D.W., and Hutchings G.J. Catal. Lett. 110 (2006) 7
179. Mori K., Hara T., Mizugaki T., Ebitani K., and Kaneda K. J. Am. Chem. Soc. 126 (2004) 10657
180. Kimmerle B., Grunwaldt J.-D., and Baiker A. Top. Catal. 44 (2007) 285
181. Abad A., Concepción P., Corma A., and García H. Angew. Chem., Int. Ed. 44 (2005) 4066
182. See Ref. 91.
183. Pushkarev V.V., Kovalchuk V.I., and D'Itri J.L. J. Phys. Chem. B 108 (2004) 5341
184. Biffis A., Cunial S., Spontoni P., and Prati L. J. Catal. (2007) 2511
185. Biffis A. J. Mol. Catal. A: Chem. 165 (2001) 303
186. Biffis A., Orlandi N., and Corain B. Adv. Mater. 15 (2003) 1551
187. Biffis A., and Sperotto E. Langmuir 19 (2003) 9548
188. Minati L., and Biffis A. Chem. Commun. (2005) 1034
189. Biffis A., and Minati L. J. Catal. 236 (2005) 405
190. Tsunoyama H., Sakurai H., Negishi Y., and Tsukuda T. J. Am. Chem. Soc. 127 (2005) 9374
191. Tsunoyama H., Sakurai H., and Tsukuda T. Chem. Phys. Lett. 429 (2006) 528
192. Tsunoyama H., Sakurai H., Ichikuni N., Negishi Y., and Tsukuda T. Langmuir 20 (2004) 11293
193. Miyamura H., Matsubara R., Miyazaki Y., and Kobayashi S. Angew. Chem., Int. Ed. 46 (2007) 4151
194. For related immobilized catalysts, see:
195. Akiyama R., and Kobayashi S. J. Am. Chem. Soc. 125 (2003) 3412
196. Okamoto K., Akiyama R., and Kobayashi S. J. Org. Chem. 69 (2004) 2871
197. Okamoto K., Akiyama R., and Kobayashi S. Org. Lett. 6 (2004) 1987
198. Okamoto K., Akiyama R., Yoshida H., Yoshida T., and Kobayashi S. J. Am. Chem. Soc. 127 (2005) 2125
199. Kobayashi S., Miyamura H., Akiyama R., and Ishida T. J. Am. Chem. Soc. 127 (2005) 9251
200. Li Z., Capretto D.A., Rahaman R.O., and He C. J. Am. Chem. Soc. 129 (2007) 12058