Amine(imine)diphosphine iron catalysts for asymmetric transfer hydrogenation of ketones and imines.

TitleAmine(imine)diphosphine iron catalysts for asymmetric transfer hydrogenation of ketones and imines.
Publication TypeJournal Article
Year of Publication2013
AuthorsZuo W, Lough AJ, Li YF, Morris RH
JournalScience (New York, N.Y.)
Volume342
Issue6162
Pagination1080-3
Date Published2013 Nov 29
Abstract

A rational approach is needed to design hydrogenation catalysts that make use of Earth-abundant elements to replace the rare elements such as ruthenium, rhodium, and palladium that are traditionally used. Here, we validate a prior mechanistic hypothesis that partially saturated amine(imine)diphosphine ligands (P-NH-N-P) activate iron to catalyze the asymmetric reduction of the polar bonds of ketones and imines to valuable enantiopure alcohols and amines, with isopropanol as the hydrogen donor, at turnover frequencies as high as 200 per second at 28°C. We present a direct synthetic approach to enantiopure ligands of this type that takes advantage of the iron(lI) ion as a template. The catalytic mechanism is elucidated by the spectroscopic detection of iron hydride and amide intermediates.

DOI10.1155/2013/587418
Alternate JournalScience