期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 41, 页码 14625-14628出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908460
关键词
C-H activation; domino reactions; heterocycles; palladium
资金
- University of Basel
- Universita degli Studi di Perugia
- MIUR
The intramolecular coupling of two C(sp(3))-H bonds to forge a C(sp(3))-C(sp(3)) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp(3))-C(sp(3)) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C-Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C-H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C-H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp(3))-C(sp(3)) bonds.
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