4.8 Article

Asymmetric Intermolecular Heck Reaction of Aryl Halides

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 2, Pages 650-652

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja412277z

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Funding

  1. Singapore National Research Foundation [NRF-RF2008-10]
  2. Nanyang Technological University

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The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates. Herein, we extend the reaction to aryl and vinyl bromides. Various cyclic olefins coupled with high enantioselectivity. Only bisphosphine oxides on a Spiro backbone formed highly stereoselective Pd catalysts. The use of alcoholic solvents and alkylammonium salts were essential to promote halide dissociation from neutral arylpalladium complexes.

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