The reaction of grignard reagents with bunte salts: A thiol-free synthesis of sulfides

Organic Letters

Volumn 16, Issue 4, 2014, Pages 1196-1199

  Reeves, Jonathan T ^a   Camara, Kaddy ^a   Han, Zhengxu S ^a   Xu, Yibo ^a   Lee, Heewon ^a   Busacca, Carl A ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SULFIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; SULFIDES;

EID: 84894598940     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500067f     Document Type: Article

References (50)

1. Bunte, H. Chem. Ber. 1874, 7, 646-648
2. Distler, H. Angew. Chem., Int. Ed. 1967, 6, 544-553
3. Milligan, B.; Swan, J. M. Rev. Pure Appl. Chem. 1962, 12, 72-94
4. Hogg, D. R. In Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 3, p 307.
5. Orzeszko, A.; Kazimierczuk, Z. Wiad. Chem. 1998, 52, 125-135
6. Price, T. S.; Twiss, D. F. J. Chem. Soc., Trans. 1909, 95, 1725-1729
7. Weiss, U.; Sokol, S. J. Am. Chem. Soc. 1950, 72, 1687-1689
8. Milligan, B.; Swan, J. M. J. Chem. Soc. 1963, 6008-6012
9. Milligan, B.; Saville, B.; Swan, J. M. J. Chem. Soc. 1961, 4850-4853
10. Milligan, B.; Saville, B.; Swan, J. M. J. Chem. Soc. 1963, 3608-3614
11. Footner, H. B.; Smiles, S. J. Chem. Soc. 1925, 2887-2891
12. Baker, R. H.; Barkenbus, C. J. Am. Chem. Soc. 1936, 58, 262-264
13. Labukas, J. P.; Drake, T. J. H.; Ferguson, G. S. Langmuir 2010, 26, 9497-9505
14. Hiver, P.; Dicko, A.; Paquer, D. Sulfur Lett. 1995, 18, 267-272
15. Prinsep, M. R. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier Science, B.V.: Amsterdam, The Netherlands, 2003; Vol. 28, pp 617-751.
16. Rakitin, O. A. Sci. Synth. 2007, 31a, 975-1000
17. Peach, M. E. In The Chemistry of the Thiol Group; Patai, S., Ed.; John Wiley & Sons: London, 1974; pp 721-784.
18. Yin, J.; Pidgeon, C. Tetrahedron Lett. 1997, 38, 5953-5954
19. Beletskaya, I. P.; Ananikov, D. P. Chem. Rev. 2011, 111, 1596-1636
20. Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590-608
21. Bichler, P.; Love, J. A. Top. Organomet. Chem. 2010, 31, 39-64
22. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544
23. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220
24. Bordwell, F. G.; Boutan, P. J. J. Am. Chem. Soc. 1957, 79, 717-722
25. Klose, W.; Schwarz, K. J. Heterocycl. Chem. 1982, 19, 1165-1167
26. Tazaki, M.; Nagahama, S.; Takagi, M. Chem. Lett. 1988, 339-1342
27. Shimazaki, M.; Takahashi, M.; Komatsu, H.; Ohta, A.; Kajii, K.; Kodama, Y. Synthesis 1992, 555-557
28. Dunst, C.; Metzger, A.; Zaburdaeva, E. A.; Knochel, P. Synthesis 2011, 21, 3453-3462
29. Alcaraz, M.-L.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O'Beirne, D.; Patel, Z. M.; Perkins, J.; Rowan, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Org. Process Res. Dev. 2005, 9, 555-569
30. Wood, W. F.; Fisher, C. O.; Graham, G. A. J. Chem. Ecol. 1993, 19, 837-841
31. Devos, M.; Patte, F.; Rouault, J.; Lafort, P.; Van Gemert, L. J. Standardized Human Olfactory Thresholds. Oxford: IRL Press at Oxford University Press, 1990; p 118.
32. Zhan, Z.; Zhang, Y. Synth. Commun. 1998, 28, 493-497
33. Zhan, Z.; Zhang, Y.; Ma, Z. J. Chem. Res. 1998, 130-131
34. Baumgarten, P. Ber. 1930, 63, 1330-1335
35. Tanaka, T.; Nakamura, H.; Tamura, Z. Chem. Pharm. Bull. 1974, 22, 2725-2728
36. Lecher, H. Z.; Hardy, E. M. J. Org. Chem. 1955, 20, 475-487
37. Jansa, P.; Cechova, L.; Dracinsky, M.; Janeba, Z. RSC Adv. 2013, 3, 2650-2654
38. Yi, J.; Fu, Y.; Xiao, B.; Cui, W.-C.; Guo, Q.-X. Tetrahedron Lett. 2011, 52, 205-208
39. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13-31
40. Barton, T. J.; Zika, R. G. J. Org. Chem. 1970, 35, 1729-1733
41. Stang, P. J.; Christensen, S. B. J. Org. Chem. 1981, 46, 823-824
42. Aida, T.; Chan, T. H.; Harpp, D. N. Tetrahedron Lett. 1981, 22, 1089-1092
43. Trofimov, B. A.; Amosova, S. V.; Gusarova, N. K.; Musorin, G. K. Tetrahedron 1982, 38, 713-718
44. Takikawa, Y.; Shimada, K.; Matsumoto, H.; Tanabe, H.; Takizawa, S. Chem. Lett. 1983, 1351-1354
45. Silveira, C. C.; Rinaldi, F.; Bassaco, M. M.; Guadagnin, R. C.; Kaufman, T. S. Synthesis 2009, 3, 469-473
46. Potapov, V. A.; Trofimov, B. A. Sci. Synth. 2006, 24, 957-1005
47. Brandsma, L.; Arens, J. F. Recl. Trav. Chim. Pays-Bas 1962, 81, 539-548
48. Silveira, C. C.; Rinaldi, F.; Guadagnin, R. C.; Braga, A. L. Synthesis 2009, 3, 469-473
49. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336
50. Barbosa, E. G.; Bega, L. A. S.; Beatriz, A.; Sarkar, T.; Hamel, E.; do Amaral, M. S.; de Lima, D. P. Eur. J. Med. Chem. 2009, 44, 2685-2688