LiCl-mediated preparation of functionalized benzylic indium(III) halides and highly chemoselective palladium-catalyzed cross-coupling in a protic cosolvent

Angewandte Chemie - International Edition

Volumn 48, Issue 12, 2009, Pages 2236-2239

  Chen, Yi Hung ^a   Sun, Mai ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Biaryls; Cross coupling; Organoindium reagents; Palladium

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; FUNCTIONAL GROUPS; INDIUM;

BENZYLIC; BIARYLS; CHEMICAL EQUATIONS; CHEMO-SELECTIVE; CO SOLVENTS; CROSS-COUPLING; ELECTROPHILES; FUNCTIONALIZED; OH GROUPS; ORGANOINDIUM REAGENTS; PALLADIUM CATALYZED CROSS COUPLINGS; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS;

PALLADIUM;

EID: 61949486112     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805588     Document Type: Article

References (67)

1. A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004.
2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516;
3. Angew. Chem. Int. Ed. 2005, 44, 4442.
4. a) X. Yang, X. Dou, K. Müllen, Chem. Asian J. 2008, 3, 759;
5. b) A. C. Grimsdale, K. Müllen, Macromol. Rapid Commun. 2007, 28, 1676;
6. c) J. Kim, T. M. Swager, Nature 2001, 411, 1030.
7. A. O. King, N. Yasuda in Organometallics in Process Chemistry (Ed.: R. D. Larsen), Springer, Berlin, 2004, pp. 205-246.
8. For recent reviews, see a) A. Suzuki, Boronic Acids. Preparation and Applications in Organic Synthesis and Medicine (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2005;
9. b) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
10. c) G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275.
11. A. Giroux, Tetrahedron Lett. 2003, 44, 233.
12. For recent reviews, see a) S. Araki, T. Hirashita in Comprehensive Organo-metallic Chemistry III, Vol. 9 (Ed.: P. Knochel), Pergamon, Oxford, 2007, p. 650;
13. b) J. Augé, N. Lubin-Germain, J. Uziel, Synthesis 2007, 1739;
14. c) T.-P. Loh, G.-L. Chua, Chem. Commun. 2006, 2739.
15. a) I. Pérez, J. P. Sestelo, L. A. Sarandeses, Org. Lett. 1999, 1, 1267;
16. b) I. Pérez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155;
17. c) M. A. Pena, I. Pérez, J. P. Sestelo, L. A. Sarandeses, Chem. Commun. 2002, 2246;
18. d) M. A. Pena, J. P. Sestelo, L. A. Sarandeses, Synthesis 2003, 780;
19. e) for a recent review, see M. A. Pena, J. P. Sestelo, L. A. Sarandeses, Synthesis 2005, 485, and references therein;
20. f) M. A. Pena, J. P. Sestelo, L. A. Sarandeses, J. Org. Chem. 2007, 72, 1271;
21. g) R. Riveiros, L. Saya, J. P. Sestelo, L. A. Sarandeses, Eur. J. Org. Chem. 2008, 1959;
22. h) J. Caeiro, J. P. Sestelo, L. A. Sarandeses, Chem. Eur. J. 2008, 14, 741;
23. i) Á. Mosquera, R. Riveiros, J. P. Sestelo, L. A. Sarandeses, Org. Lett. 2008, 10, 3745;
24. j) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738;
25. k) K. Takami, H. Yorimitsu, H. Shinokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997;
26. l) P. H. Lee, S. Sung, K. Lee, Org. Lett. 2001, 3, 3201;
27. m) B. Gotov, J. Kaufmann, H. Schumann, H.-G. Schmalz, Synlett 2002, 361;
28. n) N. Jaber, D. Gelman, H. Schumann, S. Dechert, J. Blum, Eur. J. Org. Chem. 2002, 1628;
29. o) K. Lee, J. Lee, P. H. Lee, J. Org. Chem. 2002, 67, 8265;
30. p) K. Lee, D. Seomoon, P. H. Lee, Angew. Chem. 2002, 114, 4057;
31. Angew. Chem. Int. Ed. 2002, 41, 3901;
32. q) K. Takami, H. Yorimitsu, K. Oshima, Org. Lett. 2002, 4, 2993;
33. r) H. Lee, S. W. Lee, K. Lee, Org. Lett. 2003, 5, 1103;
34. s) K. Takami, S. Mikami, H. Yorimitsu, H. Shinokubo, K. Oshima, J. Org. Chem. 2003, 68, 6627;
35. t) P. H. Lee, S. W. Lee. D. Seomoon, Org. Lett. 2003, 5, 4963;
36. u) E. Font-Sanchis, F. J. Céspedes-Guirao, Á. Sastre-Santos, F. Fernández-Lázaro, J. Org. Chem. 2007, 72, 3589.
37. a) Y.-H. Chen, P. Knochel, Angew. Chem. 2008, 120, 7760;
38. Angew. Chem. Int. Ed. 2008, 47, 7648;
39. b) V. Papoian, T. Minehan, J. Org. Chem. 2008, 73, 7376.
40. a) L. S. Chupak, J. P. Wolkowski, Y. A. Chantigny, J. Org. Chem. 2008, DOI: JO802280M;
41. b) B. Neumüller, Z. Anorg. Allg. Chem. 1991, 592, 42;
42. c) N. Fujiwara, Y. Yamamoto, J. Org. Chem. 1999, 64, 4095.
43. a) A. Krasovskiy, B. F. Straub, P. Knochel, Angew. Chem. 2006, 118, 165;
44. Angew. Chem. Int. Ed. 2006, 45, 159;
45. b) iPrMgCl·LiCl in THF is now available from Chemetall (Frankfurt, Germany).
46. a) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907;
47. Angew. Chem. Int. Ed. 2004, 43, 1871;
48. b) R. Martin, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3844;
49. c) T. E. Barder, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 5096;
50. d) M. R. Biscoe, T. E. Barder, S. L. Buchwald, Angew. Chem. 2007, 119, 7370;
51. Angew. Chem. Int. Ed. 2007, 46, 7232;
52. e) D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438;
53. Angew. Chem. Int. Ed. 2008, 47, 6338.
54. 2.
55. The reactions provided almost the same yield when water or ethanol was used as the cosolvent, but we have found that more homodimer was generated in the reaction mixture when water was used as the cosolvent. As a consequence of the solubility of some aryl iodides in THF, a mixture of THFand EtOH (6:1) was the prefered reaction medium for cross-coupling at 25-30°C.
56. The reaction gave only 52% yield when it was performed in 6:1 THF/EtOH.
57. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456.
58. C.-H. Wong, Carbohydrate-Based Drug Discovery, Wiley-VCH, Weinheim, 2003.
59. a) N. Kikuchi, H. Fujikura, S. Tazawa, T. Yamato, M. Isaji, PCT Int. Appl. WO2004113359, 2004;
60. Chem. Abstr. 2004, 142, 94061;
61. b) N. Fushimi, S. Yonekubo, H. Muranaka, H. Shiohara, H. Teranishi, K. Shimizu, F. Ito, M. Isaji, PCT Int. Appl. WO2004087727, 2004;
62. Chem. Abstr. 2004, 141, 332411;
63. c) H. Fujikura, T. Nishimura, K. Katsuno, M. Isaji, PCT Int. Appl. WO2004058790, 2004;
64. Chem. Abstr. 2004, 141, 123854;
65. d) N. Fushimi, F. Ito, M. Isaji, PCT Int. Appl. WO2003011880, 2003;
66. Chem. Abstr. 2003, 138, 153771.
67. Y. S. Lee, E. S. Rho, Y. K. Min, B. T. Kim, K. H. Kim, J. Carbohydr. Chem. 2001, 20, 503.