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

A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O 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 su...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-04, Vol.2015 (12), p.2706-2717
Main Authors: Rokade, Balaji V., Gadde, Karthik, Prabhu, Kandikere Ramaiah
Format: Article
Language:English
Subjects:
Alcohols
Amides
Azides
Chemo­selectivity
Copper
Synthetic methods
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Summary:A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O 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 ω‐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 β‐amino acids. A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O 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 also been adapted to the preparation of azides directly from their corresponding alcohols.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500010