Palladium-catalyzed oxidative carbonylation of alkyl and aryl indium reagents with CO under mild conditions

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9429-9433

  Zhao, Yingsheng ^a   Jin, Liqun ^a   Li, Peng ^a   Lei, Aiwen ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBONYLATION; CARBOXYLIC ACIDS; CATALYSIS; FUNCTIONAL GROUPS; HYDROGEN; NONMETALS; ORGANIC ACIDS; PALLADIUM;

CARBOXYLIC ACID DERIVATIVES; CATALYTIC REACTIONS; CLASSICAL METHODS; ENOLATE; GRIGNARD REAGENTS; LOW TEMPERATURE (LTR); MECHANISTIC STUDIES; MILD CONDITIONS; ORGANOINDIUM REAGENTS; OXIDATIVE ADDITION (OA); OXIDATIVE CARBONYLATION; REACTION CONDITIONS; TAUTOMERIZATION;

INDIUM;

ALKYL GROUP; CARBON MONOXIDE; CHLORIDE; GRIGNARD REAGENT; HYDROGEN; INDIUM; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; GRIGNARD REACTION; LOW TEMPERATURE; OXIDATION; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; STRUCTURE ANALYSIS; TAUTOMERIC SHIFT;

EID: 47749112915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801116s     Document Type: Article

References (63)

1. Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331.
2. Colquhoun, H. M., Thompson, D. J., Twigg, M. V., Eds. Carbonylation. Direct Synthesis of Carbonyl Compounds; 1991.
3. Skoda-Foldes, R.; Kollar, L. Curr. Org. Chem. 2002, 6, 1097-1119.
4. Magerlein, W.; Beller, M.; Indolese, A. F. J. Mol. Catal. A: Chem. 2000, 156, 213-221.
5. Magerlein, W.; Indolese, A. F.; Beller, M. Angew. Chem., Int. Ed. 2001, 40, 2856-2859.
6. Cai, C.; Rivera, N. R.; Balsells, J.; Sidler, R. R.; McWilliams, J. C.; Shultz, C. S.; Sun, Y. Org. Lett. 2006, 8, 5161-5164.
7. Blaser, H.-U.; Diggelmann, M.; Meier, H.; Naud, F.; Scheppach, E.; Schnyder, A.; Studer, M. J. Org. Chem. 2003, 68, 3725-3728.
8. Kormos, C. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 65-68.
9. Beller, M. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; 2002; Vol. 1, pp 145-156.
10. Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532-534.
11. Albaneze-Walker, J.; Bazaral, C.; Leavey, T.; Dormer, P. G.; Murry, J. A. Org. Lett. 2004, 6, 2097-2100.
12. Woell, J. B.; Fergusson, S. B.; Alper, H. J. Org. Chem. 1985, 50, 2134-2136.
13. Luh, T.-Y.; Leung, M.-k.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
14. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
15. Imbeaux, M.; Mestdagh, H.; Moughamir, K.; Rolando, C. J. Chem. Soc., Chem. Commun. 1992, 1678-1679.
16. Urata, H.; Hu, N. X.; Maekawa, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 4733-4736.
17. Urata, H.; Goto, D.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 3091-3094.
18. Urata, H.; Kinoshita, Y.; Asanuma, T.; Kosukegawa, O.; Fuchikami, T. J. Org. Chem. 1991, 56, 4996-4999.
19. Urata, H.; Maekawa, H.; Takahashi, S.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320-4322.
20. Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4407-4410.
21. Urata, H.; Kosukegawa, O.; Ishii, Y.; Yugari, H.; Fuchikami, T. Tetrahedron Lett. 1989, 30, 4403-4406.
22. Takeuchi, R.; Tsuji, Y.; Fujita, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1989, 54, 1831-1836.
23. Hashem, K. E.; Woell, J. B.; Alper, H. Tetrahedron Lett. 1984, 25, 4879-4880.
24. Heck, R. F.; Breslow, D. S. J. Am. Chem. Soc. 1963, 85, 2779-2782.
25. Zhou, H.; Lu, S.; Li, H.; Chen, J.; Fu, H.; Wang, H. J. Mol. Catal. A: Chem. 1997, 116, 329-333.
26. Ryu, I. Chem. Soc. Rev. 2001, 30, 16-25.
27. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991-2069.
28. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194.
29. Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1051-1066.
30. Fukuyama, T.; Inouye, T.; Ryu, I. J. Organomet. Chem. 2007, 692, 685-690.
31. Fukuyama, T.; Nishitani, S.; Inouye, T.; Morimoto, K.; Ryu, I. Org. Lett. 2006, 8, 1383-1386.
32. Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048-15049.
33. Peng, X.; Li, F.; Xia, C. Synlett 2006, 1161-1164.
34. Pri-Bar, I.; Schwartz, J. J. Org. Chem. 1995, 60, 8124-8125.
35. Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741-4750.
36. Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. Chem. Commun. 2003, 486-487.
37. Kelkar, A. A.; Kolhe, D. S.; Kanagasabapathy, S.; Chaudhari, R. V. Ind. Eng. Chem. Res. 1992, 31, 172-176.
38. Pena, M. A.; Sestelo, J. P.; Sarandeses, L. A. J. Org. Chem. 2007, 72, 1271-1275.
39. Xue, Z.; Yang, D.; Wang, C. J. Organomet. Chem. 2006, 691, 247-250.
40. Riveiros, R.; Rodriguez, D.; Perez Sestelo, J.; Sarandeses Luis, A. Org. Lett. 2006, 8, 1403-1406.
41. Croix, C.; Balland-Longeau, A.; Duchene, A.; Thibonnet, J. Synth. Commun. 2006, 36, 3261-3270.
42. Pena, M. A.; Sestelo, J. P.; Sarandeses, L. A. Synthesis 2005, 485-492.
43. Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 6627-6631.
44. Lee Phil, H.; Lee Sung, W.; Lee, K. Org. Lett. 2003, 5, 1103-1106.
45. Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155-4160.
46. Lee, P. H.; Sung, S.; Lee, K. Org. Lett. 2001, 3, 3201-3204.
47. Perez, I.; Perez Sestelo, J.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267-1269.
48. Perez, I.; Perez Sestelo, J.; Maestro, M. A.; Mourino, A.; Sarandeses, L. A. J. Org. Chem. 1998, 63, 10074-10076.
49. Lin, Y.-S.; Yamamoto, A. Organometallics 1998, 17, 3466-3478.
50. Izawa, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2004, 77, 2033-2045.
51. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326.
52. Milstein, D. Acc. Chem. Res. 1988, 21, 428-434.
53. Milstein, D. J. Chem. Soc., Chem. Commun. 1986, 817-818.
54. Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901.
55. Hidai, M.; Hikita, T.; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075-2077.
56. Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640-1651.
57. For further discussions about experimental evidence opposing path A, see the Supporting Information.
58. Moser, W. R.; Wang, A. W.; Kildahl, N. K. J. Am. Chem. Soc. 1988, 110, 2816-2820.
59. Scrivanti, A.; Beghetto, V.; Campagna, E.; Zanato, M.; Matteoli, U. Organometallics 1998, 17, 630-635.
60. Trzeciak, A. M.; Ziolkowski, J. J. Coord. Chem. Rev. 2005, 249, 2308-2322.
61. van Leeuwen, P. W. N. M.; Zuideveld, M. A.; Swennenhuis, B. H. G.; Freixa, Z.; Kamer, P. C. J.; Goubitz, K.; Fraanje, J.; Lutz, M.; Spek, A. L. J. Am. Chem. Soc. 2003, 125, 5523-5539.
62. Guin, D.; Baruwati, B.; Manorama, S. V. Org. Lett. 2007, 9, 1419-1421.
63. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336.