Publication: Room-temperature direct β-arylation of thiophenes and benzo[b]thiophenes and kinetic evidence for a Heck-type pathway
Authors
Colletto, Chiara ; Islam, Saidul ; Juliá Hernández, Francisco ; Larrosa, Igor
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Publisher
American Chemical Society
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DOI
https://doi.org/10.1021/jacs.5b12242
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info:eu-repo/semantics/article
Description
© 2016 American Chemical Society. This document is the Published, version of a Published Work that appeared in final form in Journal of the American Chemical Society. To access the final edited and published work see https://doi.org/10.1021/jacs.5b12242
Abstract
The first example of a regioselective β-arylation of benzo[b]thiophenes and thiophenes at room temperature with aryl iodides as coupling partners is reported. This methodology stands out for its operational simplicity: no
prefunctionalization of either starting material is required, the reaction is insensitive to air and moisture, and it proceeds at room temperature. The mild conditions afford wide functional group tolerance, often with complete regioselectivity and high yields, resulting in a highly efficient catalytic system. Initial mechanistic studies, including 13C and 2 H KIEs, suggest that this process occurs via a concerted carbo-palladation across the
thiophene double bond, followed by a base-assisted anti-elimination.
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Citation
J. Am. Chem. Soc. 2016, 138 (5), 1677–1683
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