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Acknowledgement is made to Merck, Umicore, the Robert A. Welch Foundation, the ACS-GCI Pharmaceutical Roundtable, the Korea Research Foundation (KRF-2007-356-E00037), and the NIH-NIGMS (RO1-GM069445) for support of this research. We thank Dr. Oliver Briel (Umicore) for donation of iridium and ruthenium salts, Prof. Xumu Zhang for donation of (R)-C3-TunePhos, and Drs. Ian Davies, Kevin Campos and Scott Shultz (Merck) for donation of (−)-tmbtp.
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Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents†
Article first published online: 28 NOV 2008
DOI: 10.1002/anie.200802938
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Bower, J., Kim, I., Patman, R. and Krische, M. (2009), Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents. Angewandte Chemie International Edition, 48: 34–46. doi: 10.1002/anie.200802938
- †
Publication History
- Issue published online: 18 DEC 2008
- Article first published online: 28 NOV 2008
- Manuscript Received: 19 JUN 2008
Funded by
- Merck
- Umicore
- Robert A. Welch Foundation
- ACS-GCI Pharmaceutical Roundtable
- Korea Research Foundation. Grant Number: KRF-2007-356-E00037
- NIH-NIGMS. Grant Number: RO1-GM069445
- Abstract
- Article
- References
- Cited By
Keywords:
- allylation;
- C
![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C coupling; - propargylation;
- transfer hydrogenation;
- vinylation
Graphical Abstract
Classical protocols for carbonyl allylation, propargylation, and vinylation typically rely upon the use of preformed allyl metal, allenyl metal, and vinyl metal reagents, respectively, mandating stoichiometric generation of metallic by-products. Through transfer hydrogenative CC coupling, carbonyl addition may be achieved from the aldehyde or alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants.
Abstract
Classical protocols for carbonyl allylation, propargylation and vinylation typically rely upon the use of preformed allyl metal, allenyl metal and vinyl metal reagents, respectively, mandating stoichiometric generation of metallic byproducts. Through transfer hydrogenative CC coupling, however, carbonyl addition may be achieved from the aldehyde or alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. Here, we review transfer hydrogenative methods for carbonyl addition, which encompass the first catalytic protocols enabling direct CH functionalization of alcohols.