Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 5, Pages 1677-1683Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b12242
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Funding
- European Research Council
- Engineering and Physical Sciences Research Council (EPSRC) [EP/I038578/2, EP/K039447/1]
- EPSRC [EP/I038578/1, EP/I038578/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/I038578/2, EP/I038578/1] Funding Source: researchfish
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The first example of a regioselective beta-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 C-13 and H-2 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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