Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds
Yu Dong1,2, Jian Yang1,2, Shuai He3
1Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences Chengdu 610041 P. R. China Jiyuwang@cioc.ac.cn.
Abstract:
A metal-free cross-dehydrogenative coupling of quinones with toluene derivatives has been established. A series of quinones were subjected to reaction with toluene derivatives in the presence of di-tertbutyl peroxide (DTBP) for direct synthesis of benzylquinones. The method exhibits good functional group tolerance, and desired products were obtained in moderate to good yields. Meanwhile, a radical pathway was proposed to describe the cross-dehydrogenative coupling of quinones with toluene derivatives.
Related Concept Videos
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
Reactions at the Benzylic Position: Oxidation and Reduction
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Radical Oxidation of Allylic and Benzylic Alcohols

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
