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.
| Original language | English |
|---|---|
| Pages (from-to) | 16756-16758 |
| Number of pages | 3 |
| Journal | Journal of the American Chemical Society |
| Volume | 132 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - Dec 1 2010 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Direct hydrogenation of amides to alcohols and amines under mild conditions. / Balaraman, Ekambaram; Gnanaprakasam, Boopathy; Shimon, Linda J W; Milstein, David.
In: Journal of the American Chemical Society, Vol. 132, No. 47, 01.12.2010, p. 16756-16758.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Direct hydrogenation of amides to alcohols and amines under mild conditions
AU - Balaraman, Ekambaram
AU - Gnanaprakasam, Boopathy
AU - Shimon, Linda J W
AU - Milstein, David
PY - 2010/12/1
Y1 - 2010/12/1
N2 - 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.
AB - 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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U2 - 10.1021/ja1080019
DO - 10.1021/ja1080019
M3 - Article
VL - 132
SP - 16756
EP - 16758
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 47
ER -