Redox‐Neutral Coupling between Two C(sp 3 )−H Bonds Enabled by 1,4‐Palladium Shift for the Synthesis of Fused Heterocycles | Zendy

Rocaboy Ronan | Zendy; Anastasiou Ioannis | Zendy; Baudoin Olivier | Zendy

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Redox‐Neutral Coupling between Two C(sp 3 )−H Bonds Enabled by 1,4‐Palladium Shift for the Synthesis of Fused Heterocycles

Author(s) -

Rocaboy Ronan,

Anastasiou Ioannis,

Baudoin Olivier

Publication year - 2019

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201908460

Subject(s) - chemistry , intramolecular force , aryl , bond cleavage , bromide , palladium , aniline , photochemistry , medicinal chemistry , vinyl bromide , stereochemistry , catalysis , organic chemistry , alkyl

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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