An Economical and Convenient Synthesis of Vinyl Sulfones

Zheng-Hui Guan; Wei Zuo; Lian-Biao Zhao; Zhi-Hui Ren; Yong-Min Liang

doi:10.1055/s-2007-966039

PAPER

An Economical and Convenient Synthesis of Vinyl Sulfones

Zheng-Hui Guan, Wei Zuo, Lian-Biao Zhao, Zhi-Hui Ren, Yong-Min Liang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: liangym@lzu.edu.cn;

Abstract

All articles of this category

Abstract

A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst.

Key words

vinyl sulfones - sulfinic acid sodium salts - dibromides - synthesis

Full Text

References

<A NAME="RF03007SS-1A">1a</A> Li H. Song J. Liu X. Deng L. J. Am. Chem. Soc. 2005, 127: 8948

<A NAME="RF03007SS-1B">1b</A> Lin Y.-S. Ali BE. Alper H. J. Am. Chem. Soc. 2001, 123: 7719

<A NAME="RF03007SS-1C">1c</A> Gao Y. Lam Y. Org. Lett. 2006, 8: 3283

<A NAME="RF03007SS-1D">1d</A> Zhao MM. Qu C. Lynch JE. J. Org. Chem. 2005, 70: 6944

<A NAME="RF03007SS-1E">1e</A> Babu G. Orita A. Otera J. Org. Lett. 2005, 7: 4641

<A NAME="RF03007SS-1F">1f</A> Clique B. Vassiliou S. Monteiro N. Balme G. Eur. J. Org. Chem. 2002, 1493

<A NAME="RF03007SS-1G">1g</A> Das I. Pathak T. J. Org. Chem. 2005, 70: 8047

<A NAME="RF03007SS-1H">1h</A> Caturla F. Nijera C. Tetrahedron Lett. 1997, 38: 3789

<A NAME="RF03007SS-1I">1i</A> Díez D. García P. Marcos IS. Garrido NM. Basabe P. Broughton HB. Urones JG. Tetrahedron 2005, 61: 699

<A NAME="RF03007SS-1J">1j</A> Díez D. García P. Marcos IS. Basabe P. Garrido NM. Broughtonb HB. Urones JG. Tetrahedron 2005, 61: 11641

<A NAME="RF03007SS-1K">1k</A> Scheidt KA. Roush WR. McKerrow JH. Selzer PM. Hansell E. Rosenthal P. J. Bioorg. Med. Chem. 1998, 6: 2477

<A NAME="RF03007SS-1L">1l</A> Alonso I. Carretero JC. Garrido JL. Magro V. Pedregal C. J. Org. Chem. 1997, 62: 5682

<A NAME="RF03007SS-1M">1m</A> Evans P. Leffray M. Tetrahedron 2003, 59: 7973

<A NAME="RF03007SS-2A">2a</A> Fuchs PL. Braish TF. Chem. Rev. 1986, 86: 903

<A NAME="RF03007SS-2B">2b</A> Carr RVC. Williams RV. Paquette LA. J. Org. Chem. 1983, 48: 4976

<A NAME="RF03007SS-2C">2c</A> Grimaud L. Rotulo D. Perez RR. Azam LG. Prunet J. Tetrahedron Lett. 2002, 43: 7477

<A NAME="RF03007SS-2D">2d</A> Fuchi N. Doi T. Harada T. Urban J. Cao B. Kahnc M. Takahashi T. Tetrahedron Lett. 2001, 42: 1305

<A NAME="RF03007SS-2E">2e</A> Farthing CN. Marsden SP. Tetrahedron Lett. 2000, 41: 4235

<A NAME="RF03007SS-2F">2f</A> Collins MA. Jones DN. Tetrahedron 1996, 52: 8795

<A NAME="RF03007SS-3A">3a</A> Wnuk SF. Garcia PI. Wang Z. Org. Lett. 2004, 6: 2047

<A NAME="RF03007SS-3B">3b</A> Farhat S. Marek I. Angew. Chem. Int. Ed. 2002, 41: 1410

<A NAME="RF03007SS-3C">3c</A> McCarthy JR. Huber EW. Le TB. Laskovics FM. Matthews DP. Tetrahedron 1996, 52: 45

<A NAME="RF03007SS-3D">3d</A> Kim SH. Jin Z. Ma S. Fuchs PL. Tetrahedron Lett. 1995, 36: 4013

<A NAME="RF03007SS-3E">3e</A> Nájera C. Yus M. Tetrahedron 1999, 55: 10547

<A NAME="RF03007SS-4">4</A> Palmer JT. Rasnick D. Klaus JL. Brömme D. J. Med. Chem. 1995, 38: 3193

<A NAME="RF03007SS-5">5</A> Frankel BA. Bentley M. Kruger RG. McCafferty DG. J. Am. Chem. Soc. 2004, 126: 3404

<A NAME="RF03007SS-6A">6a</A> Orita A. Katakami M. Yasui Y. Kurihara A. Otera J. Green Chem. 2001, 3: 13

<A NAME="RF03007SS-6B">6b</A> Magnier E. Tordeux M. Goumont R. Magder K. Wakselman C. J. Fluorine Chem. 2003, 124: 55

<A NAME="RF03007SS-6C">6c</A> Kroll FEK. Morphy R. Rees D. Gani D. Tetrahedron Lett. 1997, 38: 8573

<A NAME="RF03007SS-6D">6d</A> Brace NO. J. Org. Chem. 1993, 58: 4506

<A NAME="RF03007SS-7A">7a</A> Back TG. Collins S. J. Org. Chem. 1981, 46: 3249

<A NAME="RF03007SS-7B">7b</A> Liu LK. Chi Y. Jen KY. J. Org. Chem. 1980, 45: 406

<A NAME="RF03007SS-7C">7c</A> Nair V. Augustine A. Suja TD. Synthesis 2002, 2259

<A NAME="RF03007SS-7D">7d</A> Zhu S. Qin C. Xu G. Chu Q. Tetrahedron Lett. 1998, 39: 5265

<A NAME="RF03007SS-7E">7e</A> Nair V. Augustine A. George TG. Nair LG. Tetrahedron Lett. 2001, 42: 6763

<A NAME="RF03007SS-7F">7f</A> Nájera G. Baldó B. Yus M. J. Chem. Soc., Perkin Trans. 1 1988, 1029

<A NAME="RF03007SS-7G">7g</A> Sas W. J. Chem. Soc., Chem. Commun. 1984, 862

<A NAME="RF03007SS-8A">8a</A> Liu X. Duan X. Pan Z. Han Y. Liang Y. Synlett 2005, 1752

<A NAME="RF03007SS-8B">8b</A> Edwards GL. Muldoon CA. Sinclair DJ. Tetrahedron 1996, 52: 7779

<A NAME="RF03007SS-9A">9a</A> Reddick JJ. Cheng J. Roush WR. Org. Lett. 2003, 5: 1967

<A NAME="RF03007SS-9B">9b</A> Popoff IC. Dever JL. Leader GR. J. Org. Chem. 1969, 34: 1128

<A NAME="RF03007SS-10A">10a</A> Huang X. Duan D. Zheng W. J. Org. Chem. 2003, 68: 1958

<A NAME="RF03007SS-10B">10b</A> Huang X. Duan DH. Chem. Commun. 1999, 1741

<A NAME="RF03007SS-11A">11a</A> Back TG. Collin S. Krishna MV. Law KW. J. Org. Chem. 1987, 52: 4258

<A NAME="RF03007SS-11B">11b</A> Watanabe S. Yamamoto K. Itagaki Y. Iwamura T. Iwama T. Kataoka T. Tanabe G. Muraoka O. J. Chem. Soc., Perkin Trans. 1 2001, 239

<A NAME="RF03007SS-11C">11c</A> Back TG. Bethell RJ. Parvez M. Wehrli D. J. Org. Chem. 1998, 63: 7908

<A NAME="RF03007SS-12A">12a</A> Cacchi S. Fabrizi G. Goggiamani A. Parisi LM. Bernini R. J. Org. Chem. 2004, 69: 5608

<A NAME="RF03007SS-12B">12b</A> Kabalka GW. Guchhait SK. Tetrahedron Lett. 2004, 45: 4021

<A NAME="RF03007SS-13A">13a</A> Michrowska A. Bieniek M. Kim M. Klajn R. Grela K. Tetrahedron 2003, 59: 4525

<A NAME="RF03007SS-13B">13b</A> Grela K. Bieniek M. Tetrahedron Lett. 2001, 42: 6425

<A NAME="RF03007SS-14A">14a</A> Wang G. Yao SQ. Org. Lett. 2003, 5: 4437

<A NAME="RF03007SS-14B">14b</A> Wang G. Mahesh U. Chen GYJ. Yao SQ. Org. Lett. 2003, 5: 737

<A NAME="RF03007SS-14C">14c</A> Ochiai M. Kitagawa Y. Toyonari M. Uemura K. Oshima K. Shiro M. J. Org. Chem. 1997, 62: 8001

<A NAME="RF03007SS-14D">14d</A> Picó A. Moyano A. Pericàs MA. J. Org. Chem. 2003, 68: 5075

<A NAME="RF03007SS-14E">14e</A> Alonso-Cruz CR. León EI. Ortiz-López FJ. Rodríguez MS. Suárez E. Tetrahedron Lett. 2005, 46: 5265

<A NAME="RF03007SS-14F">14f</A> Sengupta S. Sarma DS. Mondal S. Tetrahedron: Asymmetry 1998, 9: 2311

<A NAME="RF03007SS-14G">14g</A> Xie M. Liu L. Wang J. Wang S. J. Organomet. Chem. 2005, 690: 4058

<A NAME="RF03007SS-15A">15a</A> Back TG. Parvez M. Zhai H. J. Org. Chem. 2003, 68: 9389

<A NAME="RF03007SS-15B">15b</A> Kakimoto M. Kai M. Kondo K. Chem. Lett. 1982, 525

<A NAME="RF03007SS-16">16</A> Henry G. Wright GF. Org. Synth., Coll. Vol. II 1943, 2: 270

<A NAME="RF03007SS-17">17</A> Knunyant I. L. Lin’kova M. G. Veller N. L. Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 6: 1075; Chem. Abstr. 1966, 65: 12134g

<A NAME="RF03007SS-18">18</A> Sas W. J. Chem. Soc., Chem. Commun. 1984, 862