Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

被引：70

作者：

El Dine, Tharwat Mohy ^{[1
,2
]}

Evans, David ^{[1
,2
]}

Rouden, Jacques ^{[1
,2
]}

Blanchet, Jerome ^{[1
,2
]}

机构：

[1] ENSICAEN, Lab Chim Mol & Thioorgan, 6 Bd Marechal Juin, F-14050 Caen, France

[2] Univ Caen Basse Normandie, CNRS, 6 Bd Marechal Juin, F-14050 Caen, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 17期

关键词：

amides; amines; boronic acid; synthetic methods; transamidation; N-FORMYLATION; ONE-POT; ASYMMETRIC ALLYLATION; PRIMARY CARBOXAMIDES; EFFICIENT CATALYST; PEPTIDE-SYNTHESIS; CARBOXYLIC-ACIDS; AMIDE SYNTHESIS; CARBON-DIOXIDE; L-PROLINE;

D O I：

10.1002/chem.201600234

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral alpha-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Bronsted acidity of acetic acid.

引用

页码：5894 / 5898

页数：5

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