Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

Angewandte Chemie
Wai Chung FuFuk Yee Kwong

Abstract

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.

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Nov 21, 2018·Chemistry : a European Journal·Jianming YanNaohiko Yoshikai
Sep 12, 2019·Angewandte Chemie·Jeffrey M FarrellFrank Würthner
Sep 18, 2020·Chemical Communications : Chem Comm·Yichao GuYanghui Zhang
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