Premium
Copper‐Catalyzed Oxidative Transformation of Secondary Alcohols to 1,5‐Disubstituted Tetrazoles
Author(s) -
Rokade Balaji V.,
Gadde Karthik,
Prabhu Kandikere Ramaiah
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300863
Subject(s) - chemistry , catalysis , copper , bond cleavage , azide , trimethylsilyl azide , oxidative phosphorylation , medicinal chemistry , perchlorate , organic chemistry , photochemistry , ion , biochemistry
A mild and convenient oxidative transformation of secondary alcohols to 1,5‐disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN 3 ) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO 4 ) 2 . 6 H 2 O] (5 mol%) and 2,3‐dichloro‐5,6‐dicyano‐ para ‐benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through CC bond cleavage.