Amide reduction
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Amide reduction in chemistry is the organic reduction of amides [1]. The main reaction product in this functional group interconversion is an amine. Reagents are lithium aluminium hydride [2][3][4][5][6], diborane and catalytic hydrogenation (requires high temperatures and pressures).
N,N-disubstituted amides can be reduced to aldehydes by using an excess of the amide:
- R(CO)NRR' + LiAlH4 → RCHO + HNRR'
With further reduction the alcohol is obtained.
Some amides can be reduced to aldehydes in the Sonn-Müller method.
Hydrosilylation
A well known method for amide reduction is hydrosilylation with silyl hydrides and a suitable catalyst based on Rh, Ru, Pt, Pd, Ir, Os, Re, Mn, Mo, In, or Ti.
Iron catalysis by triiron dodecacarbonyl in combination with polymethylhydrosiloxane has been reported [7].
External links
References
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7
- ^ Example: Organic Syntheses, Coll. Vol. 4, p.339 (1963); Vol. 39, p.19 (1959). Link
- ^ Example: Organic Syntheses, Coll. Vol. 4, p.354 (1963); Vol. 33, p.32 (1953). Link
- ^ Example: Organic Syntheses, Coll. Vol. 4, p.564 (1963); Vol. 36, p.48 (1956). Link
- ^ Example: Organic Syntheses, Coll. Vol. 6, p.382 (1988); Vol. 54, p.88 (1974). Link
- ^ Example: Organic Syntheses, Coll. Vol. 7, p.41 (1990); Vol. 61, p.24 (1983). Link
- ^ Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. (2009). "A Convenient and General Iron-Catalyzed Reduction of Amides to Amines". Angewandte Chemie (International ed. in English) 48 (50): NA. doi:10.1002/anie.200904677. PMID 19784999.
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