Para-coupling of phenols with C2/C3-substituted benzothiophene S-oxides

He, Zhen, Biremond, Tony, Perry, Gregory J.P. and Procter, David J. (2020) Para-coupling of phenols with C2/C3-substituted benzothiophene S-oxides. Tetrahedron, 76 (51), [131315]. (doi:10.1016/j.tet.2020.131315).

Record type: Article

Abstract

C2 and C3 substituted benzothiophenes are common structures in medicinal and materials chemistry. The cross-coupling of phenols with benzothiophenes is a useful route towards these important molecules. In this report we reveal an efficient C–H/C–H-type cross-coupling of benzothiophenes, activated as their S-oxides, with phenols to give C2/C3 arylated benzothiophenes. Whereas previous reports describe cross-coupling at the ortho-position between phenols and sulfoxides, this procedure allows para-functionalization of phenols that typically have their ortho positions blocked.

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Accepted/In Press date: 25 May 2020

e-pub ahead of print date: 29 May 2020

Published date: 9 December 2020

Additional Information: Funding Information: We thank the EPSRC ( EP/M005062/1 ; Postdoctoral Fellowship to Z. H.; Established Career Fellowship to D. J. P.) and The University of Manchester (Lectureship to G. J. P. P.).

Keywords: benzothiophene, cross-coupling, phenol, pummerer, sulfoxide