O-Alkyl S-3,3-dimethyl-2-oxobutyl dithiocarbonates as versatile sulfur-transfer agents in radical C(sp3)-H functionalization

Chemistry - An Asian Journal

Volumn 2, Issue 12, 2007, Pages 1568-1573

  Sato, Akinori ^b   Yorimitsu, Hideki ^b   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NONE

Author keywords

C h activation; C s bond formation; Dithiocarbonates; Radical reactions; Sulfur transfer

Indexed keywords

EID: 36949033660     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700251     Document Type: Article

References (34)

1. Reviews: a) Activation of Unreactive Bonds and Organic Synthesis, Topics in Organometallic Chemistry, Vol. 3 (Ed.: S. Murai), Springer, Berlin, 1999;
2. b) Reagents for Direct Functionalization of C-H Bonds (Ed.: P. L. Fuchs), John Wiley & Sons, Chichester, 2007;
3. (c) Handbook of C - H Transformations: Applications in Organic Synthesis (Ed.: G. Dyker), John Wiley & Sons, Chichester, 2005;
4. (d) Activation and Functionalization of C - H Bonds (Eds.: K. I. Goldberg, A. S. Goldman), American Chemical Society, Washington, D.C., 2004.
5. a) L. Feray, N. Kuznetsov, P. Renaud in Radicals in Organic Synthesis, Vol. 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, chap. 3.6;
6. b) J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, John Wiley & Sons, Chichester. 1995, chap. 18.
7. a) J. Xiang, W. Jiang, J. Gong, P. L. Fuchs, J. Am. Chem. Soc. 1997, 119, 4123-4129;
8. b) T. Yoshimitsu, Y. Arano, H. Nagaoka, J. Org. Chem. 2005, 70, 2342-2345, and references therein;
9. (c) K. Yamada, Y. Yamamoto, K. Tomioka, J. Synth. Org. Chem. Jpn. 2004, 62, 1158-1165;
10. (d) B. P. Roberts, Chem. Soc. Rev. 1999, 28, 25-35;
11. e) A. L. J. Beckwith, Chem. Soc. Rev. 1993, 22, 143-151;
12. f) K. Hirao, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 2002, 43, 3617-3620;
13. g) S. Kim, N. Kim, W.-J. Chung, C. H. Cho, Synlett 2001, 937-940;
14. h) M. Fernandez, R. Alonso, Org. Lett. 2003, 5, 2461-2464.
15. a) T. Katsuki in Radicals in Organic Synthesis, Vol. 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, chap. 2.2;
16. b) C. Limberg, Angew. Chem. 2003, 115, 6112-6136; Angew. Chem. Int. Ed. 2003, 42, 5932-5954;
17. (c) P. R. Schreiner, A. A. Fokin, Chem. Rec. 2004, 3, 247-257;
18. (d) A. A. Fokin, P. R. Schreiner, Chem. Rev. 2002, 102, 1551-1593;
19. e) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal 2001, 343, 393-427.
20. a) S. Sakaguchi, Y. Nishiwaki, T. Kitamura, Y. Ishii, J. Org. Chem. 2002, 67, 5663-5668;
21. b) F. Risi, A.-M. Alstanei, E. Volanschi, M. Carles, L. Pizzala, J.-P. Aycard, Eur. J. Org. Chem. 2000, 617-626.
22. See reference [4c,d] ; see also: A. A. Fokin, P. R. Schreiner, Adv. Synth. Catal. 2003, 345, 1035-1052.
23. a) Y. Ishii, K. Matsunaka, S. Sakaguchi, J. Am. Chem. Soc. 2000, 122, 7390-7391;
24. b) N. Basickes, T. E. Hogan, A. Sen, J. Am. Chem. Soc. 1996, 118, 13111-13112;
25. (c) S. Mukhopadhyay, A. T. Bell, Adv. Synth. Catal. 2004, 346, 913-916.
26. Quiclet-Sire and Zard reported that cyclohexane serves as a radical hydrogen donor to reduce dithiocarbonates of sugar derivatives and described that O-alkyl S-cyclohexyl dithiocarbonates were formed as by-products, although the yields of the by-products were not reported: B. Quiclet-Sire, S. Z. Zard, J. Am. Chem. Soc. 1996, 118, 9190-9191.
27. Intramolecular C-H functionalization to form C-S bonds: D. J. Pasto, F. Cottard, Tetrahedron Lett. 1994, 55, 4303-4306.
28. a) S. Z. Zard, Angew. Chem. 1997, 109, 724-737; Angew. Chem. Int. Ed. Engl. 1997, 36, 672-685;
29. b) S. Z. Zard in Radicals in Organic Synthesis, Vol. 1 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, chap. 1.6.
30. Y. Uenoyama, O. Nobuta, A. Hibi, I. Ryu, H. Yasuda, 87th Spring Meeting of the Chemical Society of Japan, 2007, 1C6-37.
31. M. von Seebach, S. I. Kozhushkov, H. Schill, D. Frank, R. Boese, J. Benet-Buchholz, D. S. Yufit, A. de Meijere, Chem. Eur. J. 2007, 13, 167-177.
32. The use of 1-bromohexane resulted in lower yields.
33. a) G. W. Gokel, K. A. Arnold, M. Delgado, L. Echeverria, V. J. Gatto, D. A. Gustowski, J. Hernandez, A. Kaifer, S. R. Miller, L. Echegoyen, Pure Appl. Chem. 1988, 60, 461-465;
34. b) G. W. Gokel, Chem. Soc. Rev. 1992, 21, 39-47.