929030-18-2Relevant academic research and scientific papers
Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions
Kong, Wangqing,Wang, Qian,Zhu, Jieping
, p. 3987 - 3991 (2017/03/27)
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.
New chiral N-heterocyclic carbene ligands in palladium-catalyzed α-arylations of amides: Conformational locking through allylic strain as a device for stereocontrol
Jia, Yi-Xia,Katayev, Dmitry,Bernardinelli, Gerald,Seidel, Thomas M.,Kuendig, E. Peter
supporting information; scheme or table, p. 6300 - 6309 (2010/07/14)
New Enders/Herrmann-type chiral N-heterocyclic carbene (NHC) ligands have been developed and applied in asymmetric palladium-catalyzed intramolecular α-arylations of amides. The best ligands feature the bulky tert-butyl group and ortho-substituted aryl gr
IBiox[(-)-menthyl]: A sterically demanding chiral NHC ligand
Wuertz, Sebastian,Lohre, Claudia,Froehlich, Roland,Bergander, Klaus,Glorius, Frank
supporting information; experimental part, p. 8344 - 8345 (2009/10/24)
(Figure Presented) An exceedingly sterically demanding, rigid, and chiral NHC ligand, IBiox[(-)-menthyl] (1), was prepared and structurally characterized. With a buried volume of 50percent, this ligand arguably represents one of the most sterically demanding monodentate ligands. The ability to use aryl chloride substrates in intramolecular palladium-catalyzed ,-arylations reveals its unique reactivity. Moreover, C2-symmetric 1 allows the highly enantioselective formation of oxindoles withup to 99percent ee.
Matching the chirality of monodentate N-heterocyclic carbene ligands: A case study on well-defined palladium complexes for the asymmetric α-arylation of amides
Luan, Xinjun,Mariz, Ronaldo,Robert, Carine,Gatti, Michele,Blumentritt, Sascha,Linden, Anthony,Dorta, Reto
supporting information; experimental part, p. 5569 - 5572 (2009/06/18)
(Chemical Equation Presented) N-Heterocyclic carbene ligands derived from C2-symmetric diamines with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)C) are prepared. These compounds e
Bulky chiral carbene ligands and their application in the palladium- catalyzed asymmetric intramolecular α-arylation of amides
Kuendig, E. Peter,Seidel, Thomas M.,Jia, Yi-Xia,Bernardinelli, Gerald
, p. 8484 - 8487 (2008/09/18)
(Chemical Equation Presented) Bring on the big cats: New, C 2-symmetric bulky N-heterocyclic carbene ligands bring major improvements in the palladium-catalyzed asymmetric intramolecular α-arylation of amides to give oxindoles (see picture, dba=trans,trans- dibenzylideneacetone), which are formed in high yield and excellent enantiomeric purity.
