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

Rokade, Balaji V and Gadde, Karthik and Prabhu, Kandikere Ramaiah (2015) Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (12). pp. 2706-2717.

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Abstract

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.

Item Type:	Journal Article
Publication:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Publisher:	WILEY-V C H VERLAG GMBH
Additional Information:	Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Keywords:	Synthetic methods; Chemoselectivity; Alcohols; Azides; Amides; Copper
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	15 Jun 2015 07:20
Last Modified:	15 Jun 2015 07:20
URI:	http://eprints.iisc.ac.in/id/eprint/51654

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