Amide reduction
Amide reduction in chemistry is the organic reduction of amides.[1] The main reaction product in this functional group interconversion is an amine. The reducing agents able to affect this reaction include lithium aluminium hydride,[2][3][4][5][6] lithium borohydride in mixed solvents of tetrahydrofuran and methanol,[7] 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.[8]
External links
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
