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

Wai Chung Fu; Zheng Wang; Wesley Ting Kwok Chan; Zhenyang Lin; Fuk Yee Kwong

doi:10.1002/anie.201703551

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

Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7166-7170. doi: 10.1002/anie.201703551. Epub 2017 May 16.

Authors

Wai Chung Fu¹, Zheng Wang², Wesley Ting Kwok Chan¹, Zhenyang Lin², Fuk Yee Kwong^{1

3}

Affiliations

¹ Department of Applied Biology and Chemical Technology & SKLC, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, Hong Kong.
² Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, Hong Kong.
³ Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, Hong Kong.

PMID: 28510348
DOI: 10.1002/anie.201703551

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.

Keywords: C−H functionalization; cross-coupling; decarboxylation; palladium; polycyclic aromatic hydrocarbons.

Publication types

Research Support, Non-U.S. Gov't