Copper catalyzed aryl amidation between Nα-Fmoc-protected amino-acid azides and aryl boronic acids

被引：2

作者：

Kumar, L. Roopesh ^{[1
]}

Thimmalapura, Vishwanatha ^{[1
]}

Panduranga, Veladi ^{[1
]}

Mahesh, Mandipogula ^{[2
]}

Ramana, P. Venkata ^{[2
]}

Sureshbabu, Vommina V. ^{[1
]}

机构：

[1] Bangalore Univ, Peptide Res Lab, Dept Studies Chem, Cent Coll Campus, Bangalore 560001, Karnataka, India

[2] Sri Krishnadevaraya Univ, Dept Chem, Anantapur, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 04期

关键词：

Amide bond; aryl boronic acid; copper(I) bromide dimethyl sulfide; N-alpha-Fmoc-amino-acid azides; CROSS-COUPLING REACTIONS; AMIDE BOND FORMATION; TOTAL CHEMICAL-SYNTHESIS; STAUDINGER LIGATION; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; CARBOXYLIC-ACIDS; SULFONYL AZIDES; THIO ACIDS; PEPTIDE;

D O I：

10.1080/00397911.2019.1704008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method for the synthesis of aryl amides via oxidative copper-catalyzed coupling of commercially available aryl boronic acids and bench stable N-alpha-protected amino-acid azides is reported. The potential utility of this protocol is demonstrated through a survey of diversely substituted aryl boronic acids and several side-chain functionalized amino-acid azides, leading to the preparation of the desired amidated products in good to excellent yields. This amide synthesis is suitable for the preparation of amides (such as peptide aryl amides and sterically hindered amino acids) that are not or hardly accessible via classical approaches.

引用

页码：506 / 515

页数：10

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