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Water as a Hydride Source in Palladium‐Catalyzed Enantioselective Reductive Heck Reactions
Author(s) -
Kong Wangqing,
Wang Qian,
Zhu Jieping
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700195
Subject(s) - chemistry , enantioselective synthesis , palladium , hydride , catalysis , heck reaction , intramolecular force , ligand (biochemistry) , deuterium , aryl , medicinal chemistry , combinatorial chemistry , organic chemistry , hydrogen , receptor , biochemistry , physics , alkyl , quantum mechanics
Pd‐catalyzed intramolecular asymmetric carbopalladation of N ‐aryl acrylamides followed by reduction of C(sp 3 )‐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 (Cat 2 B 2 ), 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.