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. 2019 Oct 28;58(44):15675-15679.
doi: 10.1002/anie.201908319. Epub 2019 Sep 24.

Metal-Free Synthesis of Benzothiophenes by Twofold C-H Functionalization: Direct Access to Materials-Oriented Heteroaromatics

Jiajie Yan  1 , Alexander P Pulis  1 , Gregory J P Perry  1 , David J Procter  1
Affiliations

Metal-Free Synthesis of Benzothiophenes by Twofold C-H Functionalization: Direct Access to Materials-Oriented Heteroaromatics

Jiajie Yan et al. Angew Chem Int Ed Engl. .

Abstract

Due to their ubiquity in nature and frequent use in organic electronic materials, benzothiophenes are highly sought after. Here we set out an unprecedented procedure for the formation of benzothiophenes by the twofold vicinal C-H functionalization of arenes that does not require metal catalysis. This one-pot annulation proceeds through an interrupted Pummerer reaction/[3,3]-sigmatropic rearrangement/cyclization sequence to deliver various benzothiophene products. The procedure is particularly effective for the rapid synthesis of benzothiophenes from non-prefunctionalized polyaromatic hydrocarbons (PAHs).

Keywords: Pummerer reaction; annulation; benzothiophene; sulfur; π-extension.

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