Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

被引：17

作者：

Rokade, Balaji V. ^{[1
]}

Gadde, Karthik ^{[1
]}

Prabhu, Kandikere Ramaiah ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 12期

关键词：

Synthetic methods; Chemoselectivity; Alcohols; Azides; Amides; Copper; C-H; DIRECT CONVERSION; OXIDATIVE TRANSFORMATION; COUPLING REACTIONS; CLICK CHEMISTRY; ORGANIC AZIDES; PRIMARY AMINES; BOND FORMATION; ALKYL AZIDES; AZIDATION;

D O I：

10.1002/ejoc.201500010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)(2)6H(2)O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of -halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to -amino acids.

引用

页码：2706 / 2717

页数：12

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