Open AccessHighly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride
Author(s) -
Yiting Gu,
Jack R. Norton,
Farbod Salahi,
Vladislav G. Lisnyak,
Zijiang Zhou,
Scott A. Snyder
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c04683
Subject(s) - chemistry , rhodium , catalysis , hydride , homogeneous , asymmetric hydrogenation , medicinal chemistry , catalytic hydrogenation , homogeneous catalysis , double bond , stereochemistry , organic chemistry , hydrogen , enantioselective synthesis , physics , thermodynamics
Under mild conditions (room temperature, 80 psi of H 2 ) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.