Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides |
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| Authors: | Wai Chung Fu Zheng Wang Dr Wesley Ting Kwok Chan Prof Dr Zhenyang Lin Prof Dr Fuk Yee Kwong |
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| Institution: | 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 |
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| 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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| Keywords: | C−H functionalization cross-coupling decarboxylation palladium polycyclic aromatic hydrocarbons |
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