Synthesis of aryl sulfides by decarboxylative C-S cross-couplings

Chemistry - A European Journal

Volumn 15, Issue 15, 2009, Pages 3666-3669

  Duan, Zhongyu ^a   Ranjit, Sadananda ^a   Zhang, Pengfei ^b   Liu, Xiaogang ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

Carboxylic acid; Cross coupling; Decarboxylation reaction; Thiols; Transition metals

Indexed keywords

ARYL SULFIDES; CATALYST SYSTEMS; CATALYZED SYNTHESIS; COUPLING PRODUCTS; COUPLING REACTIONS; CROSS-COUPLING; DECARBOXYLATION REACTION; ELEVATED TEMPERATURES; NITRO-BENZOIC ACIDS; OCTANETHIOL; STARTING MATERIALS; SYNTHESIS PROCESS; THIOLS; TRANSITION-METAL CATALYSTS;

CARBOXYLATION; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; COUPLINGS; ORGANIC ACIDS; PALLADIUM; SILVER;

TRANSITION METALS;

EID: 63849281658     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900133     Document Type: Article

References (48)

1. a) P. Metzner, A. Thuillier, Sulfur Reagents in Organic Synthesis (Eds.: A. R. Katritzky, O. Meth-Cohn, C. W. Rees), Academic Press, San Diego, 1994;
2. b) Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991;
3. c) G. De Martino, M. C. Edler, G. La Regina, A. Coluccia, M. C. Barbera, D. Barrow, R. I. Nicholson, G. Chiosis, A. Brancale, E. Hamel, M. Artico, R. Silvestri, J. Med. Chem. 2006, 49, 947-954.
4. a) A. Gangjee, Y. Zeng, T. Talreja, J. J. McGuire, R. L. Kisliuk, S. F. Queener, J. Med. Chem. 2007, 50, 3046-3053;
5. b) G. Liu, J. T. Link, Z. Pei, E. B. Reilly, S. Leitza, B. Nguyen, K. C. Marsh, G. F. Okasinski, T. W. von Geldern, M. Ormes, K. Fowler, M. Gallatin, J. Med. Chem. 2000, 43, 4025-4040;
6. c) G. Liu, J. R. Huth, E. T. Olejniczak, R. Mendoza, P. DeVries, S. Leitza, E. B. Reilly, G. F. Okasinski, S. W. Fesik, T. W. von Geldern, J. Med. Chem. 2001, 44, 1202-1210;
7. d) D. W. Hobbs, W. Clark. Still, Tetrahedron Lett. 1987, 28, 2805-2808.
8. a) M. Kosugi, T. Shimizu, T. Migita, Chem. Lett. 1978, 13-14;
9. b) J. Louie, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 11598-11599;
10. c) M. A. Fernández-Rodríguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 2180-2181;
11. d) T. Kondo, T.-A. Mitsudo, Chem. Rev. 2000, 100, 3205-3220;
12. e) C. G. Bates, R. K. Gujadhur, D. Venkataraman, Org. Lett. 2002, 4, 2803-2806;
13. f) C. G. Bates, P. Saejueng, M. Q. Doherty, D. Venkataraman, Org. Lett. 2004, 6, 5005-5008;
14. g) N. Taniguchi, J. Org. Chem. 2004, 69, 6904-6906;
15. h) S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607;
16. Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
17. i) M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397-7403;
18. J) Y.-C. Wong, T. T. Jayanth, C.-H. Cheng, Org. Lett. 2006, 8, 5613-5616;
19. k) E. Sperotto, G. P. M. van Klink, J. G. de Vries, G. van Koten, J. Org. Chem. 2008, 73, 5625-5628;
20. l) X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790-6791.
21. a) M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. 1998, 110, 688-690;
22. Angew. Chem. Int. Ed. 1998, 37, 662-664;
23. b) G. Lalic, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2003, 125, 2852-2853;
24. c) C. Peschko, C. Winklhofer, W. Steglich, Chem. Eur. J. 2000, 6, 1147-1152;
25. d) I. Shimizu, T. Yamada, J. Tsuji, Tetrahedron Lett. 1980, 21, 3199-3202;
26. e) K. Nagayama, I. Shimizu, A. Yamamoto, Chem. Lett. 1998, 1143-1144;
27. f) O. Baudoin, Angew. Chem. 2007, 119, 1395-1397;
28. Angew. Chem. Int. Ed. 2007, 46, 1373-1375;
29. g) J.-M. Becht, C. Catala, C. L. Drian, A. Wagner, Org. Lett. 2007, 9, 1781-1783;
30. h) A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250-11251;
31. i) D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323-10333;
32. j) J. Moon, M. Jeong, H. Nam, J. Ju, J. H. Moon, H. M. Jung, S. Lee, Org. Lett. 2008, 10, 945-948;
33. k) B. M. Trost, J. Y. Xu, J. Am. Chem. Soc. 2005, 127, 17180-17181;
34. l) R. Kuwano, N. Ishida, M. Murakami, Chem. Commun. 2005, 3951-3952;
35. m) J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. 2005, 117, 7084-7087;
36. Angew. Chem. Int. Ed. 2005, 44, 6924-6927;
37. n) D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044-15045;
38. o) L. J. Goossen, G. J. Deng, L. M. Levy, Science 2006, 313, 662-664;
39. p) L. J. Goossen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824-4833;
40. q) E.C. Burger, J. A. Tunge, J. Am. Chem. Soc. 2006, 128, 10002-10003;
41. r) S. R. Waetzig, J. A. Tunge, J. Am. Chem. Soc. 2007, 129, 14860-14861;
42. s) P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350-11351;
43. t) S. R. Waetzig, J. A. Tunge, Chem. Commun. 2008, 3311-3313.
44. a) D. R. Stuart, K. Fagnou, Science 2007, 316, 1172-1175;
45. b) S. Yang, B. Li, X. Wan, Z. Shi, J. Am, Chem. Soc. 2007, 129, 6066-6067.
46. I. Hutchinson, S. A. Jennings, B. R. Vishnuvajjala, A. D. Westwell, M. F. G. Stevens, J. Med. Chem. 2002, 45, 744-747.
47. D. Bernardi, L. A. Ba, G. Kirsch, Synlett 2007, 2121-2123.
48. K. Inamoto, C. Hasegawa, K. Hiroya, T. Doi, Org. Lett. 2008, 10, 5147-5150.