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Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions.
Journal article

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions.

  • Kong W Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
  • Wang Q Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
  • Zhu J Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
  • 2017-03-09
Published in:
  • Angewandte Chemie (International ed. in English). - 2017
asymmetric synthesis
deuterium labeling
hydride donors
oxindoles
reductive Heck reactions
English Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3 )-Pd intermediate using diboron-water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectivities. When heavy water was used as a deuterium donor in combination with bis(catecholato)diboron (Cat2 B2 ), deuterium was incorporated into the products with high synthetic efficiency. The ligand determined both the enantioselectivity of the reaction and the reaction pathways, thereby affording either hydroarylation (reductive Heck) or carboborylation products.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/37689
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