Generation of bis-Acyl Ketals from Esters and Benzyl Amines Under Oxidative Conditions

被引：52

作者：

Majji, Ganesh ^{[1
]}

Rajamanickam, Suresh ^{[1
]}

Khatun, Nilufa ^{[1
]}

Santra, Sourav Kumar ^{[1
]}

Patel, Bhisma K. ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 07期

关键词：

DEHYDROGENATIVE COUPLING REACTIONS; C-O BOND; CARBOXYLIC-ACIDS; CYCLIC ETHERS; ACTIVATION; ESTERIFICATION; ALDEHYDES; FUNCTIONALIZATION; ALKYLBENZENES; CYCLOALKANES;

D O I：

10.1021/jo502903d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of benzylamines with esters at an elevated temperature are expected to give amides. However, in the presence of TBAI/TBHP, esters possessing a methylene carbon alpha-to oxygen with benzylamines provide bis-esters rather than the expected amides. Benzylamines under oxidative conditions generate less nucleophilic carboxylates, which couples at the sp(3) C-H bonds of esters and cyclic ethers to give bis-acyl ketals and alpha-acyloxy ethers, respectively.

引用

页码：3440 / 3446

页数：7

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