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钌催化氨基腈的脱氨基氢化反应:直接合成1,2-氨基醇

Ruthenium-Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2-Amino Alcohols.

作者信息

Calleja Pilar, Ernst Martin, Hashmi A Stephen K, Schaub Thomas

机构信息

Catalysis Research Laboratory (CaRLa), Im Neuenheimer Feld 584, 69120, Heidelberg, Germany.

Synthesis and Homogeneous Catalysis., BASF SE, Carl-Bosch-Str. 38, 67056, Ludwigshafen, Germany.

出版信息

Chemistry. 2019 Jul 17;25(40):9498-9503. doi: 10.1002/chem.201900531. Epub 2019 Apr 17.

DOI:10.1002/chem.201900531
PMID:30848852
Abstract

A new approach for the efficient and highly selective synthesis of 1,2-amino alcohols by direct reductive hydrolysis of N-formyl-protected α-amino nitriles is reported. The commercially available RuHCl(CO)(PPh ) complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed at 55 bar of H , using a 6:1 mixture of 1,4-dioxane/water as solvent. In addition, hydroxymethyl alcohols were prepared from cyanoketones under very similar conditions.

摘要

报道了一种通过N-甲酰基保护的α-氨基腈直接还原水解高效高选择性合成1,2-氨基醇的新方法。发现市售的RuHCl(CO)(PPh )配合物是这种操作简单的方法的合适催化剂,该方法不会产生化学计量的不需要的金属废料。脱氨基氢化反应在55巴氢气压力下进行,使用1,4-二氧六环/水的6:1混合物作为溶剂。此外,在非常相似的条件下由氰基酮制备了羟甲基醇。

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