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

Research output: Journal article publicationJournal articleAcademic researchpeer-review

100 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7166-7170
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number25
DOIs
Publication statusPublished - 12 Jun 2017

Keywords

  • cross-coupling
  • C−H functionalization
  • decarboxylation
  • palladium
  • polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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