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Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions
Abstract
The selective, direct hydrogenation of amides to the corresponding alcohols and amines with cleavage of the C-N bond was discovered. The expected products of C-O cleavage are not formed (except as traces in the case of anilides). The reaction proceeds under mild pressure and neutral, homogeneous conditions using a dearomatized, bipyridyl-based PNN Ru(II) pincer complex as a catalyst. The postulated mechanism involves metal-ligand cooperation by aromatization-dearomatization of the heteroaromatic pincer core and does not involve hydrolytic cleavage of the amide. The simplicity, generality, and efficiency of this environmentally benign process make it attractive for the direct transformations of amides to alcohols and amines in good to excellent yields.
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Citations
Cited by
Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis
Gunanathan, C., & Milstein, D. (2013) · Science · doi:10.1126/science.1229712 · Cited by 1,542
Self-citationGunanathan, C., & Milstein, D. (2011) · Accounts of Chemical Research · doi:10.1021/ar2000265 · Cited by 1,078
Self-citationEarth-abundant transition metal catalysts for alkene hydrosilylation and hydroboration
Obligacion, J. V., & Chirik, P. J. (2018) · Nature Reviews Chemistry · doi:10.1038/s41570-018-0001-2 · Cited by 893
Klankermayer, J., Wesselbaum, S., Beydoun, K., & Leitner, W. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201507458 · Cited by 856
Dub, P. A., & Ikariya, T. (2012) · ACS Catalysis · doi:10.1021/cs300341g · Cited by 386
Metadata
- Authors
- Balaraman, E., Gnanaprakasam, B., Shimon, L. J. W., & Milstein, D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-11-04
- Volume
- 132
- Issue
- 47
- Pages
- 16756-16758
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2048503721
- Cited by
- 435
- References
- 0
- FWCI
- 21.35
- Type
- journal article
- Language
- en
- Open access
- closed
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- Balaraman, E., Gnanaprakasam, B., Shimon, L. J. W., & Milstein, D. (2010). Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions. Journal of the American Chemical Society. https://doi.org/10.1021/ja1080019
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