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Issue 74, 2020
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Copper-catalyzed double C–S bond formation for the synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes

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Abstract

An efficient domino process is developed for the synthesis of diversely substituted 2,3-dihydrobenzo[b]thiophenes from 2-iodoketones using a Cu-catalyst and easily available xanthate as a sulfur surrogate in good yields. This domino method has been expanded for the synthesis of 2-acylbenzo[b]thiophenes using in situ generated iodine (I2) from by-product KI in high yields. Treatment of xanthate with the copper(II)-catalyst reduced it to a Cu(I)-catalyst, which initiates the catalytic cycle. A possible mechanism has been proposed based on the results from XPS-analysis, an iodine color test and several other control experiments.

Graphical abstract: Copper-catalyzed double C–S bond formation for the synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes

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Article information


Submitted
05 Jul 2020
Accepted
04 Aug 2020
First published
05 Aug 2020

Chem. Commun., 2020,56, 10906-10909
Article type
Communication

Copper-catalyzed double C–S bond formation for the synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes

S. Sangeetha and G. Sekar, Chem. Commun., 2020, 56, 10906
DOI: 10.1039/D0CC04647G

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