4.8 Article

Transfer of Aryl Halide to Alkyl Halide: Reductive Elimination of Alkylhalide from Alkylpalladium Halides Containing syn-β-Hydrogen Atoms

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 52, Pages 14533-14537

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408341

Keywords

elimination; iodine; ligand effects; palladium; synthetic methods

Funding

  1. 973 Program [2012CB821600]
  2. Natural Science Foundation of China

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beta-Hydride abstraction is a well-accepted elementary step for catalytic cycles in organometallic chemistry. It is usually anticipated that alkylpalladium halides containing syn-beta-hydrogen atoms will undergo beta-hydride abstraction to afford the Heck-type products. However, this study discloses that the above general knowledge is only conditionally correct. Our experimental results demonstrate that the reductive elimination of alkylhalides from alkylpalladium halides containing syn-beta-hydrogen atoms may surpass the beta-hydride abstraction or even become exclusive in certain cases.

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