Palladium-catalyzed asymmetric phosphination. scope, mechanism, and origin of enantioselectivity

…, TJ Brunker, C Scriban, BJ Anderson…

Index: Blank, Natalia F.; Moncarz, Jillian R.; Brunker, Tim J.; Scriban, Corina; Anderson, Brian J.; Amir, Omar; Glueck, David S.; Zakharov, Lev N.; Golen, James A.; Incarvito, Christopher D.; Rheingold, Arnold L. Journal of the American Chemical Society, 2007 , vol. 129, # 21 p. 6847 - 6858

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Citation Number: 78

Abstract

Asymmetric cross-coupling of aryl iodides (ArI) with secondary arylphosphines (PHMe (Ar'), Ar'=(2, 4, 6)-R3C6H2; R= i-Pr (Is), Me (Mes), Ph (Phes)) in the presence of the base NaOSiMe3 and a chiral Pd catalyst precursor, such as Pd ((R, R)-Me-Duphos)(trans- stilbene), gave the tertiary phosphines PMe (Ar')(Ar) in enantioenriched form. Sterically demanding secondary phosphine substituents (Ar') and aryl iodides with electron- ...