A New Catalytic CC Bond-Forming Hydrogenation: Reductive Coupling of Dienes and Glyoxals under Catalytic Hydrogenation Conditions

Since the discovery of catalytic homogeneous hydrogenation in 1938, CC bond formation has only been observed under hydrogenation conditions in alkene hydroformylation and Fischer–Tropsch‐type processes, that is, in catalytic processes involving migratory insertion of carbon monoxide. As revealed in...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 42; no. 34; pp. 4074 - 4077
Main Authors Jang, Hye-Young, Huddleston, Ryan R., Krische, Michael J.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 05.09.2003
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
CC coupling
hydrogenation
Physical Sciences
reduction
rhodium
Science & Technology
C-C coupling
ALDEHYDES
hydrogenation
STEREOSELECTIVE HYDROFORMYLATION
SELECTIVE HYDROGENATION
ALLYLIC ALCOHOLS
ALDOL REACTION
FISCHER-TROPSCH SYNTHESIS
TITANIUM CATALYST
reduction
CATIONIC RHODIUM COMPLEXES
NICKEL-COMPLEX
CYCLIZATION
rhodium
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Summary:Since the discovery of catalytic homogeneous hydrogenation in 1938, CC bond formation has only been observed under hydrogenation conditions in alkene hydroformylation and Fischer–Tropsch‐type processes, that is, in catalytic processes involving migratory insertion of carbon monoxide. As revealed in the present study, organometallic intermediates obtained upon diene hydrogenation are subject to electrophilic trapping by glyoxal partners, thus demonstrating catalytic CC bond formation under hydrogenation conditions in the absence of carbon monoxide (see scheme). DCE: 1,2‐dichloroethane. R=aryl, heteroaryl, alkyl.
Bibliography:This research was supported in part by the Research Corporation Cottrell Scholar Award (CS0927), the Alfred P. Sloan Foundation, the Dreyfus Foundation, and Eli Lilly. We thank Dr. Ben Shoulders for skillful assistance in the characterization of deuterated materials by one- and two-dimensional 1H NMR analysis. We thank Dr. Vincent Lynch for skillful assistance in the characterization of 2 a by X-ray crystallographic analysis.
ark:/67375/WNG-JSHT0MMC-2
ArticleID:ANIE200351986
istex:E31331965C29861CC812723BEDE6AA371C7AA3BA
This research was supported in part by the Research Corporation Cottrell Scholar Award (CS0927), the Alfred P. Sloan Foundation, the Dreyfus Foundation, and Eli Lilly. We thank Dr. Ben Shoulders for skillful assistance in the characterization of deuterated materials by one‐ and two‐dimensional
1
H NMR analysis. We thank Dr. Vincent Lynch for skillful assistance in the characterization of
by X‐ray crystallographic analysis.
2 a
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351986