Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols

Yang, Kevin, Pulis, Alexander P., Perry, Gregory J.P. and Procter, David J. (2018) Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols. Organic Letters, 20 (23), 7498-7503. (doi:10.1021/acs.orglett.8b03267).

Record type: Article

Abstract

We report a transition-metal-free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene S-oxides to provide C3-arylated benzofuran products. The products from this approach can undergo subsequent functionalization to gain access to a range of important benzofuran derivatives.

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Published date: 7 December 2018

Additional Information: Funding Information: We thank the EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1) and the University of Manchester (Lectureships to A.P.P. and G.J.P.P). We thank the Manchester X-ray crystallography service. Publisher Copyright: © Copyright 2018 American Chemical Society.