4.8 Article

Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 6, Pages 2828-2832

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011036

Keywords

aryl halides; aryl sulfonates; Heck reaction; nickel catalysis; reductive Heck reaction

Funding

  1. Peking University Shenzhen Graduate School
  2. GlaxoSmithKline
  3. Singapore Economic Development Board Trust Fund (2017 GSK-EDB Green and Sustainable Manufacturing Award)
  4. A*STAR Science and Engineering Research Council [A1783c0010]
  5. Shenzhen Bay Laboratory Institute of Chemical Biology
  6. Nanyang Technological University

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The nickel-catalyzed intermolecular Heck reaction of cycloalkenes with aryl triflates, mesylates, and tosylates shows excellent enantiomeric ratios. Additionally, the asymmetric reductive Heck reaction is also applicable to a 2-cyclopentenone ketal, equivalent to conjugate arylation of the enone itself.
Nickel-catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2-cyclopentenone ketal, which is equivalent to conjugate arylation of the enone itself.

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