Asymmetric hydrosilylation of aryl ketones catalyzed by copper hydride complexed by nonracemic biphenyl bis-phosphine ligands

Bruce H Lipshutz; Kevin Noson; Will Chrisman; Asher Lower

doi:10.1021/ja021391f

Asymmetric hydrosilylation of aryl ketones catalyzed by copper hydride complexed by nonracemic biphenyl bis-phosphine ligands

J Am Chem Soc. 2003 Jul 23;125(29):8779-89. doi: 10.1021/ja021391f.

Authors

Bruce H Lipshutz¹, Kevin Noson, Will Chrisman, Asher Lower

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu

PMID: 12862472
DOI: 10.1021/ja021391f

Abstract

When complexed by selected ligands in either the BIPHEP or the SEGPHOS series, CuH is an extremely reactive catalyst capable of effecting asymmetric hydrosilylations of aromatic ketones at temperatures between -50 and -78 degrees C. Inexpensive silanes serve as stoichiometric sources of hydride. Substrate-to-ligand ratios exceeding 100000:1 have been documented. The level of induction is usually in the >90% ee category. The nature of the reagent has been investigated using spectroscopic and chemical means, although its composition remains unclear.