Copper-Catalyzed Asymmetric Hydrogenation of Aryl and Heteroaryl Ketones

High throughput screening enabled the development of a Cu-based catalyst system for the asymmetric hydrogenation of prochiral aryl and heteroaryl ketones that operates at H2 pressures as low as 5 bar. A ligand combination of (R,S)-N-Me-3,5-xylyl-BoPhoz and tris(3,5-xylyl)phosphine provided benzylic...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 15; no. 17; pp. 4560 - 4563
Main Authors Krabbe, Scott W, Hatcher, Mark A, Bowman, Roy K, Mitchell, Mark B, McClure, Michael S, Johnson, Jeffrey S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2013
Amer Chemical Soc
Subjects
Benzyl Alcohols - chemical synthesis
Benzyl Alcohols - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Copper - chemistry
Hydrogenation
Ketones - chemical synthesis
Ketones - chemistry
Ligands
Molecular Structure
Phosphines - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
SYSTEM
EFFICIENT ENANTIOSELECTIVE HYDROSILYLATION
TEMPERATURE
CONJUGATE REDUCTION
COMPLEXES
<(PH3P)CUH>6
AMINOPHOSPHINE LIGANDS
AIR
ALDEHYDES
REVERSAL
Online AccessGet full text

Cover

More Information
Summary:High throughput screening enabled the development of a Cu-based catalyst system for the asymmetric hydrogenation of prochiral aryl and heteroaryl ketones that operates at H2 pressures as low as 5 bar. A ligand combination of (R,S)-N-Me-3,5-xylyl-BoPhoz and tris(3,5-xylyl)phosphine provided benzylic alcohols in good yields and enantioselectivities. The electronic and steric characteristics of the ancillary triarylphosphine were important in determining both reactivity and selectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4021223