Synthesis 2014; 46(19): 2608-2616
DOI: 10.1055/s-0034-1378318
paper
© Georg Thieme Verlag Stuttgart · New York

Tandem Thioetherification Reactions of 2-(2,2-Dibromovinyl)phenol Derivatives with Thiophenols and Thiols

Haobing Geng
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   Email: zhxiuli@163.com
,
Juan Du
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   Email: zhxiuli@163.com
,
Shanshan Chen
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   Email: zhxiuli@163.com
,
Qinghua Huang
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   Email: zhxiuli@163.com
,
Xiuli Zhang*
a   Department of Chemistry, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China   Email: zhxiuli@163.com
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
,
Lei Wang*
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
c   Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China   Email: leiwang@chnu.edu.cn   Fax: +86(561)3090518
› Author Affiliations
Further Information

Publication History

Received: 26 March 2014

Accepted after revision: 22 May 2014

Publication Date:
24 June 2014 (online)


Abstract

A tandem thioetherification reaction of 2-(2,2-dibromovinyl)phenol derivatives with thiophenols and thiols has been developed. In the presence of potassium hydroxide, 2-(2,2-dibromovinyl)phenols reacted with thiophenols and thiols to generate 2-arylthiobenzofurans and 2-alkylthiobenzofurans in good yields in N,N-dimethylformamide via a one-pot tandem reaction. This method has several advantages including commercial availability of starting materials, simple operation, and easy purification of products.

Supporting Information

 
  • References

    • 1a Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C. Eur. J. Med. Chem. 2008; 43: 300
    • 1b Kurosawa W, Kan T, Fukuyama T. J. Am. Chem. Soc. 2003; 125: 8112
    • 1c Trost BM, Tang W. Angew. Chem. Int. Ed. 2002; 41: 2795
    • 2a Du H.-A, Zhang X.-G, Tang R.-Y, Li J.-H. J. Org. Chem. 2009; 74: 7844
    • 2b Carril M, SanMartin R, Tellitu I, Domínguez E. Org. Lett. 2006; 8: 1467
    • 2c Findlay JA, Buthelezi S, Li G, Seveck M, Miller JD. J. Nat. Prod. 1997; 60: 1214
    • 2d Nakamura M, Ilies L, Otsubo S, Nakamura E. Org. Lett. 2006; 8: 2803
    • 2e Rizzo S, Rivière C, Piazzi L, Bisi A, Gobbi S, Bartolini M, Andrisano V, Morroni F, Tarozzi A, Monti J.-P, Rampa A. J. Med. Chem. 2008; 51: 2883

      For a review, see:
    • 3a Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893

    • For selected examples, see:
    • 3b Manarin F, Roehrs JA, Gay RM, Brandão R, Menezes PH, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 2153
    • 3c Zhao B, Lu X. Org. Lett. 2006; 8: 5987
    • 4a Okitsu T, Nakazawa D, Taniguchi R, Wada A. Org. Lett. 2008; 10: 4967
    • 4b Fürstner A, Heilmann EK, Davies PW. Angew. Chem. Int. Ed. 2007; 46: 4760
    • 4c Nakamura I, Mizushima Y, Yamamoto Y. J. Am. Chem. Soc. 2005; 127: 15022
    • 4d Liao Y, Smith J, Fathi R, Yang Z. Org. Lett. 2005; 7: 2707
  • 5 Guo X, Yu R, Li H, Li Z. J. Am. Chem. Soc. 2009; 131: 17387
    • 6a Wang S, Li P, Yu L, Wang L. Org. Lett. 2011; 13: 5968
    • 6b Li C, Zhang Y, Li P, Wang L. J. Org. Chem. 2011; 76: 4692

      For a review, see:
    • 7a Chelucci G. Chem. Rev. 2012; 112: 1344

    • For selected examples, see:
    • 7b Jouvin K, Bayle A, Legrand F, Evano G. Org. Lett. 2012; 14: 1652
    • 7c Wang Z.-J, Yang F, Lv X, Bao W. J. Org. Chem. 2011; 76: 967
    • 7d Rao ML. N, Jadhav DN, Dasgupta P. Org. Lett. 2010; 12: 2048
    • 7e Newman SG, Lautens M. J. Am. Chem. Soc. 2010; 132: 11416
    • 7f Bryan CS, Braunger JA, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 7064
    • 7g Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
    • 7h Arthuis M, Pontikis R, Florent J.-C. Org. Lett. 2009; 11: 4608
    • 7i Bryan CS, Lautens M. Org. Lett. 2008; 10: 4633
  • 8 Nagamochi M, Fang Y.-Q, Lautens M. Org. Lett. 2007; 9: 2955
    • 9a Ye S, Liu G, Pu S, Wu J. Org. Lett. 2012; 14: 70
    • 9b Qin X, Cong X, Zhao D, You J, Lan J. Chem. Commun. 2011; 47: 5611
  • 10 Thielges S, Meddah E, Bisseret P, Eustache J. Tetrahedron Lett. 2004; 45: 907
  • 11 Newman SG, Aureggi V, Bryan CS, Lautens M. Chem. Commun. 2009; 5236
  • 12 Chen W, Zhang Y, Zhang L, Wang M, Wang L. Chem. Commun. 2011; 47: 10476
    • 13a Perin G, Lenardão EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
    • 13b Singh D, Alberto EE, Rodrigues OE. D, Braga AL. Green Chem. 2009; 11: 1521
    • 13c Reddy VP, Kumar AV, Swapna K, Rao KR. Org. Lett. 2009; 11: 951
    • 13d Wang M, Ren K, Wang L. Adv. Synth. Catal. 2009; 351: 1586
    • 13e Zhao X, Yu Z, Yan S, Wu S, Liu R, He W, Wang L. J. Org. Chem. 2005; 70: 7338
    • 13f Ajiki K, Hirano M, Tanaka K. Org. Lett. 2005; 7: 4193
    • 13g Nishino T, Okada M, Kuroki T, Watanabe T, Nishiyama Y, Sonoda N. J. Org. Chem. 2002; 67: 8696

      For reviews, see:
    • 14a Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
    • 14b Mugesh G, Du Mont WW, Sies H. Chem. Rev. 2001; 101: 2125

    • For selected examples, see:
    • 14c Back TG, Moussa Z. J. Am. Chem. Soc. 2003; 125: 13455
    • 14d Braga AL, Vargas F, Sehnem JA, Braga RC. J. Org. Chem. 2005; 70: 9021
    • 15a Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915
    • 15b Taniguchi N, Onami T. Synlett 2003; 829
    • 16a Abramov MA, Dehaen W, D’hooge B, Petrov ML, Smeets S, Toppet S, Voets M. Tetrahedron 2000; 56: 3933
    • 16b Petrov ML, Androsov DA, Abramov MA, Abramova IP, Dehaen W, Lyakhovetskii YuI. Russ. J. Org. Chem. 2006; 42: 1521
    • 17a Liu J, Chen W, Ji Y, Wang L. Adv. Synth. Catal. 2012; 354: 1585
    • 17b Zhou W, Chen W, Wang L. Org. Biomol. Chem. 2012; 10: 4172
    • 17c Liu J, Li P, Chen W, Wang L. Chem. Commun. 2012; 48: 10052
  • 18 Kao H.-L, Lee C.-F. Org. Lett. 2011; 13: 5204
  • 19 Liu J, Li P, Chen W, Wang L. RSC Adv. 2013; 3: 4723