Aryne 1,2,3-Trifunctionalization with Aryl Allyl Sulfoxides.

J Am Chem Soc

School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng Street, Chongqing 400030, P. R. China.

Published: August 2016

An aryne 1,2,3-trisubstitution with aryl allyl sulfoxides is accomplished, featuring an incorporation of C-S, C-O, and C-C bonds on the consecutive positions of a benzene ring. The reaction condition is mild with broad substrate scope. Preliminary mechanistic study suggests a cascade formal [2 + 2] reaction of aryne with S═O bond, an allyl S → O migration, and a Claisen rearrangement.

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http://dx.doi.org/10.1021/jacs.6b06981DOI Listing

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