The synthesis of some 2-hydroxy-2(H)-3,3-diaryl- and 3-hydroxy-3(H)-2,2-diaryl-benzo[b]thiophens (4) and (7) respectively is described; by acidic treatment these compounds readily rearrange to 2,3-diaryl-benzo[b]thiophens (5) in almost quantitative yields.
Radical Cyclization of Arenesulfonyl Chlorides and Alkynes: A Rapid Access to π-Conjugated Benzothiophenes
作者:Danyang Wan、Yudong Yang、Xingyan Liu、Mingliang Li、Siling Zhao、Jingsong You
DOI:10.1002/ejoc.201501439
日期:2016.1
A metal-free radicalcyclization of arenesulfonylchlorides with alkynes has been developed, which provides a rapid and practical access to a variety of π-conjugated benzothiophenes with a broad reactive functional group tolerance. Furthermore, dialkynyl compounds could also undergo this transformation to give extended π-systems in good yields.