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Synlett 2011(7): 1010-1014  
DOI: 10.1055/s-0030-1259717
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient Synthesis of Multisubstituted 2-Acyl Furans via PIFA/I2-Mediated Oxidative Cycloisomerization of cis-2-En-4-yn-1-ols

Xiangwei Du, Haoyi Chen, Yifeng Chen, Jingjin Chen, Yuanhong Liu*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
e-Mail: yhliu@mail.sioc.ac.cn;
Further Information

Publication History

Received 30 November 2010
Publication Date:
08 March 2011 (online)

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Abstract

A novel oxidative cycloisomerization of cis-enynols has been developed using a combination of hypervalent iodine(III) reagent, molecular iodine, and a base. This method offers an efficient synthesis of 2-acyl furans with diverse substitution patterns in a ­regioselective manner under mild reaction conditions. A mechanistic proposal for these transformations involving alkyne activation by trifluoroacetylhypoiodite generated in situ is presented.

Key words

hypervalent iodine(III) reagent - oxidative cyclo­isomerization - enynols - 2-acyl furans - synthetic methods

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During our further study, we found that IBX-promoted cyclization of enynol 1l could proceed at r.t. to afford 2l in 90% yield.

12

We found that PIFA could also react with NaHCO3 to release iodobenzene.