Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate

An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in goo...

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Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (7), p.1670-1673
Main Authors: Sangeetha, Subramani, Sekar, Govindasamy
Format: Article
Language:English
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Summary:An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)­ethanone, which is a known pre-mRNA splicing modulator.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00462