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. The reagents are lithium aluminium hydride,[2][3][4][5][6] Ether and catalytic hydrogenation (requires high temperatures and pressures).

Reduction of amides to amines


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[edit]

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[edit]

References[edit]

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7 
  2. ^ Example: Organic Syntheses, Coll. Vol. 4, p.339 (1963); Vol. 39, p.19 (1959). Link
  3. ^ Example: Organic Syntheses, Coll. Vol. 4, p.354 (1963); Vol. 33, p.32 (1953). Link
  4. ^ Example: Organic Syntheses, Coll. Vol. 4, p.564 (1963); Vol. 36, p.48 (1956). Link
  5. ^ Example: Organic Syntheses, Coll. Vol. 6, p.382 (1988); Vol. 54, p.88 (1974). Link
  6. ^ Example: Organic Syntheses, Coll. Vol. 7, p.41 (1990); Vol. 61, p.24 (1983). Link
  7. ^ 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): 9507–9510. doi:10.1002/anie.200904677. PMID 19784999.  edit