Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 5, Pages 946-950Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300863
Keywords
alcohols; azides; copper; regioselectivity; tetrazoles
Categories
Funding
- IISc
- CSIR [01/2415/10-EMR-II]
- RL Fine Chem
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A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)(2)(.)6H(2)O] (5mol%) and 2,3-dichloro-5,6-dicyano-para-benzoquinone (DDQ) (1.2equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through CC bond cleavage.
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