Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 21, Pages 10553-10560Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5014542
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Funding
- National Basic Research Program of China [2015CB856600]
- National Natural Science Foundation of China [21472185]
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CuCl2-mediated intramolecular C-H/C-H cross-dehydrogenative coupling (CDC) of thioalkyl-substituted a-acetyl or alpha-aroyl ketene N,S-acetals afforded 2-thioalkyl indoles. Tunable C-S bond transformations of the resultant indoles led to highly functionalized N-heterocyclic compounds. A beta-thioalkyl is necessary to activate the N,S-acetal substrate and enable the CDC reaction to occur, and the relevant mechanism studies revealed that the CDC reaction follows a radical pathway.
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