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Regioselective Synthesis of Polycyclic and Heptagon‐embedded Aromatic Compounds through a Versatile π‐Extension of Aryl Halides
Author(s) -
Fu Wai Chung,
Wang Zheng,
Chan Wesley Ting Kwok,
Lin Zhenyang,
Kwong Fuk Yee
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201703551
Subject(s) - synthon , norbornadiene , chemistry , aryl , decarboxylation , halide , regioselectivity , ethylene , coupling reaction , combinatorial chemistry , catalysis , organic chemistry , alkyl
A versatile π‐extension reaction was developed based on the three‐component cross‐coupling of aryl halides, 2‐haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho ‐C−H activator and ethylene synthon via a retro‐Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.