Comprehensive Organic Synthesis 1991
DOI: 10.1016/b978-0-08-052349-1.00218-3
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Reduction of CN to CHNH by Metal Hydrides

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Cited by 85 publications
(43 citation statements)
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“…[1,2] In comparison, the corresponding reactions of C5 5N bonds have been studied much less. Although the addition to the C5 5N bond of imines, hydrazones and oximes are well known, [3] the development of such reaction is often limited by the poor electrophilicity of the C5 5N carbon atom. Numerous new reagents have been developed for the reduction of oximes to amines including NaBH4, [3,4] LiAlH 4 [5,6] and indium/acetic acid.…”
Section: Reprintsmentioning
confidence: 99%
See 1 more Smart Citation
“…[1,2] In comparison, the corresponding reactions of C5 5N bonds have been studied much less. Although the addition to the C5 5N bond of imines, hydrazones and oximes are well known, [3] the development of such reaction is often limited by the poor electrophilicity of the C5 5N carbon atom. Numerous new reagents have been developed for the reduction of oximes to amines including NaBH4, [3,4] LiAlH 4 [5,6] and indium/acetic acid.…”
Section: Reprintsmentioning
confidence: 99%
“…Although the addition to the C5 5N bond of imines, hydrazones and oximes are well known, [3] the development of such reaction is often limited by the poor electrophilicity of the C5 5N carbon atom. Numerous new reagents have been developed for the reduction of oximes to amines including NaBH4, [3,4] LiAlH 4 [5,6] and indium/acetic acid. [7] Though some of these are widely used, still they have limitations based on chemo-selectivity and economic considerations.…”
Section: Reprintsmentioning
confidence: 99%
“…Aldimines are valuable starting materials not only for different N-containing heterocycles but also to diverse secondary heteroaromatic amines (Hutchins & Hutchins, 1991), which represent good candidates for bio-screening with diverse types of activities (Kleemann & Engel, 2005;Evers et al, 2005). Thus, the N-aryl imine 6, the main and value starting, can be prepared from commercially available 3-indolaldehyde 4 and 2-cyanoaniline 5, according to published methods (Colyer et al, 2006).…”
Section: Synthesis and Purification Of The New The (3-indolmethyl)acementioning
confidence: 99%
“…Asymmetric reductive amination of carbonyl compounds [3] and direct asymmetric reductive amination [4] are convenient methods to synthesize chiral amines. The reducing agents in these methods are usually hydrogen and a catalyst [5,6] or hydride as a reducing a agent which includes NaBH 3 CN [7], borohydride exchange resin [8], silica gel/Zn (BH 4 ) [9], Et 3 SiH/CF 3 COOH [10] and H 2 SO 4 /NaBH 4 [11]. Most of these reagents deliver good yields of amines; however, their hazardous nature creates complications.…”
Section: Introductionmentioning
confidence: 99%