Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions
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 (Cat2B2), 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.
Kong, Wangqing,Wang, Qian,Zhu, Jieping
p. 3987 - 3991
(2017/03/27)
Palladium-catalyzed enantioselective α-arylation and α-vinylation of oxindoles facilitated by an axially chiral p-stereogenic ligand
(Chemical Equation Presented) The enantioselective α-arylation and α-vinylation of oxindoles catalyzed by Pd and a biarylmonophosphine ligand with both axial and phosphorus-based chirogenicity is reported. The resultant quaternary carbon stereocenters are
Taylor, Alexander M.,Altman, Ryan A.,Buchwald, Stephen L.
supporting information; experimental part
p. 9900 - 9901
(2009/12/06)
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