Tetraethylorthosilicate as a mild dehydrating reagent for the synthesis of N-formamides with formic acid

被引：20

作者：

Nishikawa, Yasuhiro ^{[1
]}

Nakamura, Hidetsugu ^{[1
]}

Ukai, Norimitsu ^{[1
]}

Adachi, Wakana ^{[1
]}

Hara, Osamu ^{[1
]}

机构：

[1] Meijo Univ, Fac Pharm, Tenpaku Ku, 150 Yagotoyama, Nagoya, Aichi 4688503, Japan

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 09期

基金：

日本学术振兴会;

关键词：

Formylation; Silicate; Dehydration; Amino acids; Amide bond; EFFICIENT CATALYST; CARBOXYLIC-ACIDS; CARBON-DIOXIDE; FORMYLATION; AMINES; TRANSAMIDATION; CARBOXAMIDES; AMIDES; ESTERS; CO2;

D O I：

10.1016/j.tetlet.2017.01.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of N-formamides with formic acid as a formyl source under mild conditions was achieved using tetraethylorthosilicate (TEOS), a low cost and environmentally benign reagent. The mild conditions in this system enable the formylation of a variety of amino acid derivatives including stereochemically labile phenylglycine ethyl ester with 96% ee. This new protocol could also be applied to simple amines including weakly basic aniline derivatives, giving various primary and secondary formamides. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：860 / 863

页数：4

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