Sulfite-Promoted One-Pot Synthesis of Sulfides by Reaction of Aryl Disulfides with Alkyl Halides

Ri-yuan Tang; Ping Zhong; Qiu-lian Lin

doi:10.1055/s-2006-950363

PAPER

Sulfite-Promoted One-Pot Synthesis of Sulfides by Reaction of Aryl Disulfides with Alkyl Halides

Ri-yuan Tang, Ping Zhong*, Qiu-lian Lin
The School of Chemistry and Material Science, Wenzhou University, Wenzhou, P. R. of China
Fax: +86(577)88373013; e-Mail: zhongp0512@163.com;

Abstract

All articles of this category

Abstract

A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products.

Key words

disulfide - sulfide - rongalite - electron transfer - one-pot reaction

Full Text

References

1 For general reviews on sulfides, see: Jones DN. In Comprehensive Organic Chemistry Vol. 3: Barton DHR. Ollis WD. Pergamon Press; Oxford: 1979. p.33-103

2 Herradura PS. Pendola KA. Guy RK. Org. Lett. 2000, 2: 2019 ; and references therein

3a Lindley J. Tetrahedron 1984, 40: 1433

3b Yunoki SI. Takimiya K. Aso Y. Otsubo T. Tetrahedron Lett. 1997, 38: 3017

3c Yin J. Pidgeon C. Tetrahedron Lett. 1997, 38: 5953

4 Shah STA. Khan KM. Heinrich AM. Voelter W. Tetrahedron Lett. 2002, 43: 8281

5a Goux C. Lhoste P. Sinou D. Tetrahedron Lett. 1992, 33: 8099

5b Page PCB. Klair SS. Brown MP. Harding MM. Smith CS. Maginn SJ. Mulley S. Tetrahedron Lett. 1998, 29: 4477

5c Li C.-J. Harpp DN. Tetrahedron Lett. 1992, 33: 7293

6 Chowdhury S. Roy S. Tetrahedron Lett. 1997, 38: 2149

7a Kwong FY. Buchwald SL. Org. Lett. 2002, 4: 3517

7b Bates CG. Gujadhur RK. Venkataraman D. Org. Lett. 2002, 4: 2803

7c Taniguchi N. Onami T. J. Org. Chem. 2004, 69: 915

8 Ranu BC. Mandal T. J. Org. Chem. 2004, 69: 5793

9 Tang RY. Zhong P. Lin QL. J. Fluorine Chem. 2006, 127: 948

10a Wakselman C. Tordeux M. Clavel JL. Langlois B. J. Chem. Soc., Chem. Commun. 1991, 993

10b Clavel JL. Langlois B. Nantermet R. Tordeux M. Wakselman C. J. Chem. Soc., Perkin Trans. 1 1992, 3371

For reviews on the application of sodium dithionite in organic synthesis, see:

11a Cho J. Sato S. Takeoka S. Tsuchida E. Macromolecules 2001, 34: 2751

11b Overberger CG. McGill EV. Anselme JP. J. Am. Chem. Soc. 1969, 91: 687

11c Hawthorne JO. Mihelic EL. Morgan MS. Wilt MH. J. Org. Chem. 1963, 28: 2831

11d Eisner U. Kuthan J. Chem. Rev. 1972, 72: 1

11e Haddadin MJ. Alkaysi HN. Saheb SE. Tetrahedron 1970, 26: 1115

11f Brimble MA. Nairn MR. J. Chem. Soc., Perkin Trans. 1 2000, 317

11g de Vries JG. Kellogg RM. J. Org. Chem. 1980, 45: 4126

11h Cao P. Duan JX. Chen QY. J. Chem. Soc., Chem. Commun. 1994, 737

11i Huang WY. Hu LQ. Ge WZ. J. Fluorine Chem. 1989, 43: 305

11j Tang XQ. Hu CM. J. Chem. Soc., Chem. Commun. 1994, 631

11k Tordeux M. Langlois B. Wakselman C. J. Chem. Soc., Perkin Trans. 1 1990, 2293

For reviews on the application of sodium dithionite in organic synthesis, see:

12a Beatriz MI. Nazario M. Carlos S. J. Org. Chem. 1997, 62: 7585

12b Liu WD. Chi CC. Pai IF. Wu AT. Chung WS. J. Org. Chem. 2002, 67: 9267

12c Liu JH. Wu AT. Huang MW. Wu CW. Chung WS. J. Org. Chem. 2000, 65: 3395

12d Huang BN. Liu JT. Huang WY. J. Chem. Soc., Perkin Trans. 1 1994, 101

12e Huang BN. Liu JT. Tetrahedron Lett. 1990, 31: 2711

12f Huang BN. Liu JT. Huang WY. J. Chem. Soc., Chem. Commun. 1990, 1781

12g William RD. Maurice M. Samia AM. Tetrahedron Lett. 2001, 42: 4811

12h Anselmi E. Blazejewski JC. Tordeux M. Wakselman C. J. Fluorine Chem. 2000, 105: 41

12i Wu FH. Huang BN. Lu L. Huang WY. J. Fluorine Chem. 1996, 80: 91

13 Tang RY. Zhong P. Lin QL. Phosphorus, Sulfur Silicon Relat. Elem. 2006, in press

14 Antonello S. Daasbjerg K. Jensen H. Taddei F. Maran F. J. Am. Chem. Soc. 2003, 125: 14905

15 Antonello S. Benassi R. Gavioli G. Taddei F. Maran F. J. Am. Chem. Soc. 2002, 124: 7529

16 Hodgson WG. Neaves A. Parker CA. Nature (London) 1956, 178: 489

17 Zheng N. McWilliams JC. Fleitz FJ. Armstrong JD. Volante RP. J. Org. Chem. 1998, 63: 9606