Synlett, Table of Contents Synlett 2014; 25(6): 843-846DOI: 10.1055/s-0033-1340672 letter © Georg Thieme Verlag Stuttgart · New York TBHP/TBAI-Promoted Oxidative Cyclization of o-Acylphenols for the Construction of 2-Aryloxybenzofuran-3(2H)-ones Hui Yu* Department of Chemistry, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China Fax: +86(21)65981097 Email: yuhui@tongji.edu.cn , Fengling Zhang Department of Chemistry, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China Fax: +86(21)65981097 Email: yuhui@tongji.edu.cn , Weihua Huang Department of Chemistry, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China Fax: +86(21)65981097 Email: yuhui@tongji.edu.cn › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract An efficient metal-free approach to 2-aryloxybenzofuranonefuran-3(2H)-ones has been developed. Using tert-butyl hydroperoxide as oxidant and tetrabutylammonium iodide as catalyst, 2-acylphenols reacted with phenols to provide 2-aminobenzofuran-3(2H)-one derivatives in moderate to good yields. Key words Key words tert-butyl hydroperoxide - TBHP - tetrabutylammonium iodide - TBAI - benzofuran-3(2H)-one - 2-acylphenol - oxidative cyclization Full Text References References and Notes 1a Hadj-esfandiari N, Navidpour L, Shadnia H, Amini M, Samadi N, Faramarzid MA, Shafiee A. Bioorg. Med. Chem. Lett. 2007; 17: 6354 1b Manjulatha K, Srinivas S, Mulakayala N, Rambabu D, Prabhakar M, Arunasree KM, Alvala M, Basaveswara MV. Bioorg. Med. Chem. Lett. 2012; 22: 6160 1c Charrier C, Clarhaut J, Gesson JP, Estiu G, Wiest O, Roche J, Bertrand P. J. Med. Chem. 2009; 52: 3112 2a Zhou G, Zhu J, Xie Z, Li Y. Org. Lett. 2008; 10: 721 2b Gormemis AE, Ha TS, Im I, Jung KY, Lee JY, Park CS, Kim YC. ChemBioChem 2005; 6: 1745 2c Venkatesan AM, Santos OD, Ellingboe J, Evrard DA, Harrison BL, Smith DL, Scerni R, Hornby GA, Schechter LE, Andree TH. Bioorg. Med. Chem. Lett. 2010; 20: 824 3a Deshpande AR, Paradkar MV. Synth. Commun. 1990; 20: 809 3b Ghosh S, Datta I, Chakraborty R, Das TK, Sengupta J, Sarkar DC. Tetrahedron 1989; 45: 1441 3c Morice C, Garrido F, Mann A, Suffert J. Synlett 2002; 501 3d Inoue A, Kitagawa K, Shinokubo H, Oshima K. J. Org. Chem. 2001; 66: 4333 3e Coe JW, Bianco KE, Boscoe BP, Brooks PR, Cox ED, Vetelino MG. J. Org. Chem. 2003; 68: 9964 3f Farran D, Bertrand P. Synth. Commun. 2012; 42: 989 4a Moriarty RM, Prakash O, Prakash I. Chem. Commun. 1984; 20: 1342 4b Fan R, Sun Y, Ye Y. Org. Lett. 2009; 11: 5174 5a Liu Z, Zhang J, Chen S, Shi E, Xu Y, Wan X. Angew. Chem. Int. Ed. 2012; 51: 3231 5b Mai WP, Wang HH, Li ZC, Yuan JW, Xiao YM, Yang LR, Mao P, Qu LB. Chem. Commun. 2012; 48: 10117 5c Xie J, Jiang H, Cheng Y, Zhu C. Chem. Commun. 2012; 48: 979 5d Uyanik M, Suzuki D, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2011; 50: 5331 5e Chen L, Shi E, Liu Z, Chen S, Wei W, Li H, Xu K, Wan X. Chem. Eur. J. 2011; 17: 4085 5f Shi E, Shao Y, Chen S, Hu H, Liu Z, Zhang J, Wan X. Org. Lett. 2012; 14: 3384 5g Ma L, Wang X, Yu W, Han B. Chem. Commun. 2011; 47: 11333 5h Huang J, Li LT, Li HY, Husan E, Wang P, Wan B. Chem. Commun. 2012; 48: 10204 5i Zhang J, Jiang J, Li Y, Wan X. J. Org. Chem. 2013; 78: 11366 5j Zhang J, Jiang J, Li Y, Zhao Y, Wan X. Org. Lett. 2013; 15: 3222 6a Lamani M, Prabhu KR. Chem. Eur. J. 2012; 18: 14638 6b Yan Y, Zhang Y, Zha Z, Wang Z. Org. Lett. 2013; 15: 2274 7a Xu K, Hu Y, Zhang S, Zha Z, Wang Z. Chem. Eur. J. 2012; 18: 9793 7b Zhang X, Wang L. Green Chem. 2012; 14: 2141 7c Wei W, Shao Y, Hu H, Zhang F, Zhang C, Xu Y, Wan X. J. Org. Chem. 2012; 77: 7157 7d Zhang J, Wang Z, Wang Y, Wan C, Zheng X, Wang Z. Green Chem. 2009; 11: 1973 7e Wang Q, Wan C, Gu Y, Zhang J, Gao L, Wang Z. Green Chem. 2011; 13: 578 7f Jiang H, Huang H, Cao H, Qi C. Org. Lett. 2010; 12: 5561 7g Wan C, Gao L, Wang Q, Zhang J, Wang Z. Org. Lett. 2010; 12: 3902 7h Zhang J, Zhu D, Yu C, Wan C, Wang Z. Org. Lett. 2010; 12: 2841 7i Yan Y, Wang Z. Chem. Commun. 2011; 47: 9513 8 Typical Experimental Procedure for the Synthesis of 2,2-Bis(4-nitrophenoxy)benzofuran-3(2H)-one (3a) In a 15 mL reaction tube a mixture of 2-acetylphenol (1a, 68 mg, 0.5 mmol), 4-nitrophenol (2a, 174 mg, 1.25 mmol), t-BuOOH (70% in H2O, 2 mmol), TBAI (55 mg, 0.15 mol) in MeCN (2.0 mL) was stirred at r.t. under air for 16 h, until complete consumption of starting material as monitored by TLC. After the reaction was finished, the mixture was quenched with sat. Na2S2O3 solution, then extracted with EtOAc, dried over anhydrous Na2SO4, and evaporated in vacuum. The residue was purified by flash column chromatography on silica gel (PE–EtOAc, 8:1) to give the product 3a. Supplementary Material Supplementary Material Supporting Information
