Synthesis 2015; 47(18): 2731-2737
DOI: 10.1055/s-0034-1380419
special topic
© Georg Thieme Verlag Stuttgart · New York

Metal-Free [3+2] Oxidative Coupling of Phenols with Alkenes: Synthesis of Dihydrobenzofurans

Yating Zhao
State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, P. R. of China   Email: xiawj@hit.edu.cn
,
Binbin Huang
State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, P. R. of China   Email: xiawj@hit.edu.cn
,
Chao Yang
State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, P. R. of China   Email: xiawj@hit.edu.cn
,
Bing Li
State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, P. R. of China   Email: xiawj@hit.edu.cn
,
Wujiong Xia*
State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, P. R. of China   Email: xiawj@hit.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 11 March 2015

Accepted after revision: 14 April 2015

Publication Date:
27 May 2015 (online)


Abstract

Herein, we demonstrated a benign and metal-free [3+2]-cycloaddition reaction using simple and readily available phenols and styrenes as substrates and sodium persulfate as an inexpensive and environmentally friendly oxidant for the direct synthesis of dihydrobenzofurans. This methodology was applied to the synthesis of corsifuran A in a single step.

Supporting Information

 
  • References

    • 1a Ortega N, Beiring B, Urban S, Glorius F. Tetrahedron 2012; 68: 5185
    • 1b Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM. J. Med. Chem. 1986; 29: 302
    • 1c Shi GQ, Dropinski JF, Zhang Y, Santini C, Sahoo SP, Berger JP, MacNaul KL, Zhou GC, Agrawal A, Alvaro R, Cai TQ, Hernandez M, Wright SD, Moller DE, Heck JV, Meinke PT. J. Med. Chem. 2005; 48: 5589
  • 2 Pieters L, Dyck SV, Gao M, Bai R, Hamel E, Vlietinck A, Lemière G. J. Med. Chem. 1999; 42: 5475
    • 3a Chauret CD, Bernard CB, Arnason JT, Durst T. J. Nat. Prod. 1996; 59: 152
    • 3b De Campos MP, Filho VC, Da Silva RZ, Yunes RA, Zaccino S, Juarez S, Bella Cruz RC, Bella Cruz A. Biol. Pharm. Bull. 2005; 28: 1527
  • 4 Gates BD, Dalidowicz P, Tebben A, Wang S, Sweton JS. J. Org. Chem. 1992; 57: 2135
    • 5a Chen MW, Gao LL, Ye ZS, Jiang GF, Zhou YG. Chem. Commun. 2013; 49: 1660
    • 5b Li QB, Zhou FT, Liu ZG, Li XF, Zhu WD, Xie JW. J. Org. Chem. 2011; 76: 7222
    • 5c Bertolini F, Crotti P, Bussolo VD, Macchia F, Pineschi M. J. Org. Chem. 2007; 72: 7761
    • 5d Kuethe JT, Wong A, Journet M, Davies IW. J. Org. Chem. 2005; 70: 3727
    • 5e Li WS, Guo ZR, Thornton J, Katipally K, Polniaszek R, Thottathil J, Vu T, Wong M. Tetrahedron Lett. 2002; 43: 1923
    • 5f Stafford JA, Valvano NL. J. Org. Chem. 1994; 59: 4346
    • 5g Meijs GF, Beckwith AL. J. J. Am. Chem. Soc. 1986; 108: 5890
    • 6a Larock RC, Yang H, Pace P, Narayanan K, Russell CE, Cacchi S, Fabrizi G. Tetrahedron 1998; 54: 7343
    • 6b Wang XS, Lu Y, Dai HX, Yu JQ. J. Am. Chem. Soc. 2010; 132: 12203
    • 6c Kshirsagar UA, Regev C, Parnes R, Pappo D. Org. Lett. 2013; 15: 3174
    • 6d Gaster E, Vainer Y, Regev A, Narute S, Sudheendran K, Werbeloff A, Shalit H, Pappo D. Angew. Chem. Int. Ed. 2015; 54: 4198
    • 7a Dohi T, Hu YJ, Kamitanaka T, Washimi N, Kita Y. Org. Lett. 2011; 13: 4814
    • 7b Li QB, Hu XC. Chem. Lett. 2012; 41: 1633
    • 8a Chiba K, Fukuda M, Kim S, Kitano Y, Tada M. J. Org. Chem. 1999; 64: 7654
    • 8b Kim S, Noda S, Hayashi K, Chiba K. Org. Lett. 2008; 10: 1827
    • 8c Okada Y, Yoshioka T, Koike M, Chiba K. Tetrahedron Lett. 2011; 52: 4690
  • 9 Dai CH, Meschini F, Narayanam JM. R, Stephenson CR. J. J. Org. Chem. 2012; 77: 4425
    • 10a Tomakinian T, Guillot R, Kouklovsky C, Vincent G. Angew. Chem. Int. Ed. 2014; 53: 11881
    • 10b Beaud R, Guillot R, Kouklovsky C, Vincent G. Angew. Chem. Int. Ed. 2012; 51: 12546
    • 10c Kirste A, Nieger M, Malkowsky IM, Stecker F, Fischer A, Waldvogel SR. Chem. Eur. J. 2009; 15: 2273
    • 10d Malkowsky IM, Rommel CE, Froehlich R, Griesbach U, Puetter H, Waldvogel SR. Chem. Eur. J. 2006; 12: 7482
    • 10e Zerbe K, Woithe K, Li DB, Vitali F, Bigler L, Robinson JA. Angew. Chem. Int. Ed. 2004; 43: 6709
  • 11 Huang ZL, Jin LQ, Feng Y, Peng P, Yi H, Lei AW. Angew. Chem. Int. Ed. 2013; 52: 7151
    • 12a Zhao GL, Yang C, Guo L, Sun HN, Chen C, Xia W. Chem. Commun. 2012; 48: 2337
    • 12b Zhao GL, Yang C, Guo L, Sun HN, Lin R, Xia W. J. Org. Chem. 2012; 77: 6302
    • 12c Sun HN, Yang C, Gao F, Li Z, Xia W. Org. Lett. 2013; 15: 624
    • 12d Guo L, Yang C, Zheng LW, Xia W. Org. Biomol. Chem. 2013; 11: 5787
    • 12e Zhao YT, Li Z, Yang C, Lin R, Xia W. Belstein J. Org. Chem. 2014; 10: 622
    • 12f Sun HN, Yang C, Lin R, Xia W. Adv. Synth. Catal. 2014; 356: 2775
  • 13 Blum TR, Zhu Y, Nordeen SA, Yoon TP. Angew. Chem. Int. Ed. 2014; 53: 11056
  • 14 Minisci F, Citterio A, Giordano C. Acc. Chem. Res. 1983; 16: 27
  • 15 Meng LK, Zhang GH, Liu C, Wu K, Lei AW. Angew. Chem. Int. Ed. 2013; 52: 10195