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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, Email:

X. Du, H. Chen, Y. Chen, J. Chen, Y. Liu, Synlett, 2011, 1010-1014.

DOI: 10.1055/s-0030-1259717

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

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Key Words

hypervalent iodine(III) reagents, PIFA, oxidative cycloisomerization, enynols, 2-acyl furans, furans, synthetic methods

ID: J60-Y2011-1080