Journal of Organic Chemistry 2010-01-01

Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Kyung Soo Yoo, Justin O'Neill, Satoshi Sakaguchi, Richard Giles, Joo Ho Lee, Kyung Woon Jung

Index: J. Org. Chem. 75(1) , 95-101, (2010)

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Abstract

Chiral dimeric tridentate NHC-amidate-alkoxide palladium(II) complexes, 3a and 3b, effected oxidative boron Heck-type reactions of aryl boronic acids with both acyclic and cyclic alkenes at room temperature to afford the corresponding coupling products with high enantioselectivities. The high degree of enantioselection, far superior to existing methods, stems from differences in the nonbonding interactions in the proposed transition states, due to the influence from bulky substituents of the alkene substrates and the "counter axial groups" of the palladium(II) catalysts.