New Procedures for Catalytic Carbophilic Activation by Gold and Gallium π-Acids

Synlett

Volumn 26, Issue 11, 2015, Pages 1427-1436

  Bour, Christophe ^a   Gandon, Vincent ^a,b  

^a UNIVERSITÉ PARIS SUD   (France)

^b CNRS   (France)

Author keywords

copper; gallium; gold; homogeneous catalysis; N heterocyclic carbenes

Indexed keywords

ALKENE; ALKYNE; CARBENE; CARBOXYLIC ACID SALT; GALLIUM PI ACID DERIVATIVE; GOLD; GOLD CHLORIDE; LEWIS ACID; ORGANOGALLIUM COMPOUND; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYTIC CARBOPHILIC ACTIVATION; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; COMPLEX FORMATION; DECOMPOSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 84931957243     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1380712     Document Type: Article

References (89)

1. Hartwig J. In Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books Sausalito, CA: 2010
2. Modern Gold Catalyzed Synthesis. Hashmi A. S. K, Toste F. D. Wiley-VCH Weinheim: 2012
3. Gold Catalysis a Homogeneous Approach. Toste F. D., Michelet V. Imperial College Press London: 2014
4. Kumar M., Jasinski J., Hammond J. B., Xu B. Chem. Eur. J.: 2014; 20 3113
5. Hashmi A. S. K, Blanco M. C., Fischer D., Bats J. W. Eur. J. Org. Chem.: 2006; 1387
6. Lemière G., Gandon V., Agenet N., Goddard J.-P, de Kozak A., Aubert C., Fenstebank L., Malacria M. Angew. Chem. Int. Ed.: 2006; 45 7596
7. Lavallo V., Wright J. H. II, Tham F. S., Quinlivan S. Angew. Chem. Int. Ed.: 2013; 52 3172
8. Blanco Jaimes M. C., Böhling C. R. N, Serrano-Becerra J. M., Hashmi A. S. K. Angew. Chem. Int. Ed.: 2013; 52 7963
9. Malhotra D., Mashuta M. S., Hammond G. B., Xu B. Angew. Chem. Int. Ed.: 2014; 53 4456
10. Blanco Jaimes M. C., Rominger F., Pereira M. M., Carrilho R. M. B, Carabineiro S. A. C, Hashmi A. S. K. Chem. Commun.: 2014; 50 4937
11. Wang D., Cai R., Sharma S., Jirak J., Thummanapelli S. K., Akhmedov N. G., Zhang H., Liu X., Petersen J. L., Shi X. J. Am. Chem. Soc.: 2012; 134 9012
12. Schmidbaur H., Schier A. Z. Naturforsch. B: 2011; 66 329
13. Weber S. G., Rominger F., Straub B. F. Eur. J. Inorg. Chem.: 2012; 2863
14. Homs A., Escofet I., Echavarren A. M. Org. Lett.: 2013; 15 5782
15. Abadie M. A., Trivelli X., Medina F., Capet F., Roussel P., Agbossou-Niedercorn F., Michon C. ChemCatChem: 2014; 6 2235
16. Wegener M., Huber F., Bolli C., Jenne C., Kirsch S. F. Chem. Eur. J.: 2015; 21 1328
17. Xi Y., Wang D., Ye X., Akhmedov N. G., Petersen J. L., Shi X. Org. Lett.: 2014; 16 306
18. Han J., Shimizu N., Lu Z., Amii H., Hammond G. B., Xu B. Org. Lett.: 2014; 16 3500
19. For a review see: Zhang S., Wei F., Song C., Jia J., Xu Z. Chin. J. Chem.: 2014; 32 937
20. P. P. Power Nature: 2010; 463 171
21. Bullock R. M. Catalysis without Precious Metals. Wiley-VCH Weinheim: 2010
22. Fürstner A., Davies P. W. Angew. Chem. Int. Ed.: 2007; 46 3410
23. Michelet V., Toullec P. Y., Genêt J.-P. Angew. Chem. Int. Ed.: 2008; 47 4268
24. Lee S. I., Chatani N. Chem. Commun.: 2009; 371
25. Melaimi M., Soleilhavoup M., Bertrand G. Angew. Chem. Int. Ed.: 2010; 49 8810
26. El-Hellani A., Bour C., Gandon V. Adv. Synth. Catal.: 2011; 353 1865
27. Petz W. Coord. Chem. Rev.: 2015; 291 1
28. Marion N., Escudero-Adán E. C., Benet-Buchholz J., Stevens E. D., Fensterbank L., Malacria M., Nolan S. P. Organometallics: 2007; 26 3256
29. El-Hellani A., Monot J., Tang S., Guillot R., Bour C., Gandon V. Inorg. Chem.: 2013; 52 11493
30. El-Hellani A., Monot J., Guillot R., Bour C., Gandon V. Inorg. Chem.: 2013; 52 506
31. Dénès F., Pérez-Luna A., Chemla F. Chem. Rev.: 2010; 110 2366
32. Zhou C.-Y, Che C.-M. J. Am. Chem. Soc.: 2007; 129 5828
33. Oliver-Meseguer J., Cabrero-Antonino J. R., Domínguez I., Leyva-Pérez A., Corma A. Science: 2012; 338 1452
34. The reason for this incompatibility is not known but it cannot be attributed to the presence of the enol system since α-aurated carbonyl complexes are stable. See: Hashmi A. S. K, Schäfer S., Wölfle M., Diez Gil C., Fischer P., Laguna A., Blanco M. C., Gimeno M. C. Angew. Chem. Int. Ed.: 2007; 46 6184
35. Guérinot A., Fang W., Sircoglou M., Bour C., Bezzenine-Lafollée S., Gandon V. Angew. Chem. Int. Ed.: 2013; 52 5848
36. Weizhen F., Presset M., Guérinot A., Bour C., Bezzenine-Lafollée S., Gandon V. Org. Synth.: 2015; 92 117
37. Fang W., Presset M., Guérinot A., Bour C., Bezzenine-Lafollée S., Gandon V. Chem. Eur. J.: 2014; 20 5439
38. Fehr C., Winter B., Magpantay I. Chem. Eur. J.: 2009; 15 9773
39. Fehr C., Vuagnoux M., Buzas A., Arpagaus J., Sommer H. Chem. Eur. J.: 2011; 17 6214
40. Rauniyar V., Wang Z. J., Burks H. E., Toste F. D. J. Am. Chem. Soc.: 2011; 133 8486
41. For the carbophilic character of TfOH, see inter alia: Rosenfeld D. C., Shekhar S., Takemiya A., Utsunomiya M., Hartwig J. F. Org. Lett.: 2006; 8 4179
42. Kamimura A., Yamane Y., Yo R., Tanaka T., Uno H. J. Org. Chem.: 2014; 79 7696
43. Itoh Y., Tsuji H., Yamagata K.-i, Endo K., Tanaka I., Nakamura M., Nakamura E. J. Am. Chem. Soc.: 2008; 130 17161
44. Fang W., Presset M., Guérinot A., Bour C., Bezzenine-Lafollée S., Gandon V. Org. Chem. Front.: 2014; 1 608
45. Huguet N., Echavarren A. M. In Asymmetric Synthesis II: More Methods and Applications. Christmann M., Bräse S. Wiley-VCH Weinheim: 2013; Chap. 26
46. Wang Y.-M, Lackner A. D., Toste F. D. Acc. Chem. Res.: 2014; 47 889
47. Osborn J. A., Jardine F. H., Young J. F., Wilkinson G. J. Chem. Soc. A: 1966; 1711
48. Schrock R. R., Osborn J. A. J. Am. Chem. Soc.: 1976; 98 2134
49. Schrock R. R., Osborn J. A. J. Am. Chem. Soc.: 1976; 98 2143
50. Schrock R. R., Osborn J. A. J. Am. Chem. Soc.: 1976; 98 4450
51. Crabtree R. H. Acc. Chem. Res.: 1979; 12 331
52. The use of AuCl3 as the catalyst for skeletal rearrangements of 1,6- and 1,7-enynes is briefly mentioned in the conclusion of: Chatani N., Morimoto T., Muto T., Murai S. J. Am. Chem. Soc.: 1994; 116 6049
53. Hashmi A. S. K, Frost T. M., Bats J. W. J. Am. Chem. Soc.: 2000; 122 11553
54. Phipps R. J., Hamilton G. L., Toste F. D. Nature Chem.: 2012; 4 603
55. For an example of a gallium complex that imitates transition-metal catalysts in π-acid catalysis, see: Fedushkin I. L., Nikipelov A. S., Morozov A. G., Skatova A. A., Cherkasov A. V., Abakumov G. A. Chem. Eur. J.: 2012; 18 255
56. For examples of well-defined organogallium complexes used as Lewis acids for molecular catalysis, see: Bour C., Gandon V. Coord. Chem. Rev.: 2014; 279 43
57. Dagorne S., Atwood D. A. Chem. Rev.: 2008; 108 4037
58. The Group 13 Metals Aluminum, Gallium, Indium and Thallium: Chemical Patterns and Peculiarities. Aldridge S., Downs A. J. John Wiley & Sons Chichester: 2011
59. Burt J., Levason W., Reid G. Coord. Chem. Rev.: 2014; 260 65
60. Fliedel C., Schnee G., Avilés T., Dagorne S. Coord. Chem. Rev.: 2014; 275 63
61. For an abnormal carbene-gallium chloride complex, see: Chen M., Wang Y., Gilliard R. J. Jr, Wei P., Schwartz N. A., Robinson G. H. Dalton Trans.: 2014; 43 14211
62. Braunschweig H., Dewhurst R. D., Hupp F., Kaufmann C., Phukan A. K., Schneider C., Ye Q. Chem. Sci.: 2014; 5 4099
63. Trinh C., Bodensteiner M., Virovets A. V., Peresypkina E. V., Scheer M., Matveev S. M., Timoshkin A. Y. Polyhedron: 2010; 29 414
64. Burt J., Levason W., Reid G. Coord. Chem. Rev.: 2014; 260 65
65. Chemistry of Hypervalent Compounds. Akiba K.-y. Wiley-VCH New York: 1999
66. Bour C., Monot J., Tang S., Guillot R., Farjon J., Gandon V. Organometallics: 2014; 33 594
67. Tang S., Monot J., El-Hellani A., Michelet B., Guillot R., Bour C., Gandon V. Chem. Eur. J.: 2012; 18 10239
68. For NHC-stabilized borenium cations, see: Do D. C. H, Muthaiah S., Ganguly R., Vidović D. Organometallics: 2014; 33 4165
69. Inoue H., Chatani N., Murai S. J. Org. Chem.: 2002; 67 1414
70. Chatani N., Inoue H., Kotsuma T., Murai S. J. Am. Chem. Soc.: 2002; 124 10294
71. Mamane V., Hannen P., Fürstner A. Chem. Eur. J.: 2004; 10 4556
72. Miyanahana Y., Chatani N. Org. Lett.: 2006; 8 2155
73. Simmons E. M., Sarpong R. Org. Lett.: 2006; 8 2883
74. Li H.-J, Guillot R., Gandon V. J. Org. Chem.: 2010; 75 8435
75. Mukaiyama T., Ohno T., Suda S., Kobayashi S. Chem. Lett.: 1991; 1059
76. Zhao J.-F, Tan B.-H, Loh T.-P. Chem. Sci.: 2011; 2 349
77. Zhuo L.-G, Zhang J.-J, Yu Z.-X. J. Org. Chem.: 2012; 79 8527
78. Surendra K., Corey E. J. J. Am. Chem. Soc.: 2014; 136 10918
79. Gupta M. K., O'Sullivan T. P. RSC Adv.: 2013; 3 25498
80. Yamaguchi M., Matsunaga S., Shibasaki M., Michelet B., Bour C., Gandon V. e-EROS: 2014; DOI: 10.1002/047084289X.rn00118u.pub3
81. Michelet B., Bour C., Gandon V. Chem. Eur. J.: 2014; 20 14488
82. See: Horn S., Albrecht M. Chem. Commun.: 2011; 47 8802; and references cited therein
83. Ranu B. C., Samanta S. J. Org. Chem.: 2003; 68 7130
84. Ranu B. C., Samanta S. Tetrahedron: 2003; 59 7901
85. Farrell J. M., Heiden Z. M., Stephan D. W. Organometallics: 2011; 30 4497
86. Bour C., Guillot R., Gandon V. Chem. Eur. J.: 2015; 21 6066
87. Michelet B., Colard-Itté J.-R, Thiery G., Guillot R., Bour C., Gandon V. Chem. Commun.: 2015; 51 7401
88. Presset M., Michelet B., Guillot R., Bour C., Bezzenine-Lafollée S., Gandon V. Chem. Commun.: 2015; 51 5318
89. Lebœuf D., Schulz E., Gandon V. Org. Lett.: 2014; 16 6464