Tetramethyl Orthosilicate (TMOS) as a Reagent for Direct Amidation of Carboxylic Acids

被引：66

作者：

Braddock, D. Christopher ^{[1
]}

Lickiss, Paul D. ^{[1
]}

Rowley, Ben C. ^{[1
]}

Pugh, David ^{[1
]}

Purnomo, Teresa ^{[1
]}

Santhakumar, Gajan ^{[1
]}

Fussell, Steven J. ^{[2
]}

机构：

[1] Imperial Coll London, Dept Chem, London SW7 2AZ, England

[2] Pfizer Ltd, Ramsgate Rd, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

AMIDE BOND FORMATION; CATALYZED DIRECT AMIDATION; ROOM-TEMPERATURE; MESOPOROUS SILICA; PEPTIDE-SYNTHESIS; COUPLING REAGENT; CONVENIENT METHOD; AMINO-ACIDS; IN-SITU; CARBOXAMIDES;

D O I：

10.1021/acs.orglett.7b03841

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.

引用

页码：950 / 953

页数：4

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