Issue 5, 2012
From the journal:

New Journal of Chemistry

Oxidative functionalization of benzylic C–H bonds by DDQ†

Victor S. Batista,*a   Robert H. Crabtree,*a   Steven J. Konezny,a   Oana R. Lucaa  and  Jeremy M. Praetoriusa  

* Corresponding authors

a Yale Chemistry Department, 225 Prospect St., New Haven, USA
E-mail: victor.batista@yale.edu, robert.crabtree@yale.edu
Fax: +1 203 432 6144
Tel: +1 203 432 6672

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).

Graphical abstract: Oxidative functionalization of benzylic C–H bonds by DDQ

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2NJ40021A
Article type
Letter
Submitted
10 Jan 2012
Accepted
17 Feb 2012
First published
08 Mar 2012

New J. Chem., 2012,36, 1141-1144

Permissions

Request permissions

Oxidative functionalization of benzylic C–H bonds by DDQ

V. S. Batista, R. H. Crabtree, S. J. Konezny, O. R. Luca and J. M. Praetorius, New J. Chem., 2012, 36, 1141 DOI: 10.1039/C2NJ40021A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements