Journal
ORGANIC LETTERS
Volume 19, Issue 7, Pages 1670-1673Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00462
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Funding
- DST New Delhi [SB/S1/OC-72/2013]
- IIT Madras
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An efficient protocol is described for the synthesis of 2-acylbenzo [b]thiophenes from easily accessible 2-iodochalcones through alpha-C-H functionalization using Cu(OAc)(2) catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothio-phenes 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.
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