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Redox-Neutral Coupling between Two C(sp3)-H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

Rocaboy, Ronan and Anastasiou, Ioannis and Baudoin, Olivier. (2019) Redox-Neutral Coupling between Two C(sp3)-H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles. Angewandte Chemie International Edition, 58 (41). pp. 14625-14628.

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Abstract

The intramolecular coupling of two C(sp3)-H bonds to forge a C(sp3)-C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)-C(sp3) 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(sp3)-C(sp3) bonds.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:17 Oct 2019 07:55
Deposited On:17 Oct 2019 07:55

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