Premium
Copper‐Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
Author(s) -
Rokade Balaji V.,
Gadde Karthik,
Prabhu Kandikere Ramaiah
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500010
Subject(s) - chemistry , azide , allylic rearrangement , chemoselectivity , trimethylsilyl azide , catalysis , organic chemistry , moiety , alcohol , combinatorial chemistry , nitrogen
A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO 4 ) 2 · 6H 2 O as a catalyst, and trimethylsilyl azide (TMSN 3 ) 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.