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仲酰胺半催化还原为亚胺和醛。

Semi-catalytic reduction of secondary amides to imines and aldehydes.

作者信息

Lee Sun-Hwa, Nikonov Georgii I

机构信息

Chemistry Department, Brock University, 500 Glenridge Ave., St. Catharines, ON L2S 3A1, Canada.

出版信息

Dalton Trans. 2014 Jun 21;43(23):8888-93. doi: 10.1039/c4dt00372a.

DOI:10.1039/c4dt00372a
PMID:24798570
Abstract

Secondary amides can be reduced by silane HSiMe2Ph into imines and aldehydes by a two-stage process involving prior conversion of amides into iminoyl chlorides followed by catalytic reduction mediated by the ruthenium complex [Cp(i-Pr3P)Ru(NCCH3)2]PF6 (1). Alkyl and aryl amides bearing halogen, ketone, and ester groups were converted with moderate to good yields under mild reaction conditions to the corresponding imines and aldehydes. This procedure does not work for substrates bearing the nitro-group and fails for heteroaromatic amides. In the case of cyano substituted amides, the cyano group is reduced to imine.

摘要

仲酰胺可通过硅烷HSiMe2Ph分两步还原为亚胺和醛,该过程包括先将酰胺转化为亚氨基酰氯,然后由钌配合物[Cp(i-Pr3P)Ru(NCCH3)2]PF6(1)介导进行催化还原。带有卤素、酮和酯基的烷基和芳基酰胺在温和的反应条件下以中等至良好的产率转化为相应的亚胺和醛。该方法不适用于带有硝基的底物,对杂芳族酰胺也不起作用。对于氰基取代的酰胺,氰基会还原为亚胺。

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