Oxidative functionalization of benzylic C-H bonds by DDQ

Authors: 
Victor S. Batista, Robert H. Crabtree, Steven J. Konezny, Oana R. Luca, and Jeremy M. Praetorius
Name of the Journal: 
New J. Chem.
Year of Publication: 
2012
Date of Publication: 
March 8, 2012
Volume: 
36
Issue: 
5
Pages: 
1141-1144
Publisher: 
The Royal Society of Chemistry
Abstract: 

C–H activation of the methyl group of toluene and related ArCH3 derivatives by 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) gives insertion products, ArCH2O[C6Cl2(CN)2]OH via a rate-determining hydride abstraction by DDQ. The resulting benzylic ether can undergo reactions with phosphines to give benzylic phosphonium salts (Wittig reagents) and with phosphites to give phosphonate esters (Horner–Wadsworth–Emmons reagents).

DOI link: 
10.1039/C2NJ40021A