/   Home   /   Newsroom   /   Research News

SIOC Made Progress in the C–H Functionalization via Electrochemical Oxidation

Mar 09, 2017     Email"> PrintText Size

Palladium-catalyzed C–H funtionalization reaction is a powerful chemical transformation. And reductive elimination from metal centers is a key step in a myriad of carbon–carbon and carbon–heteroatom bond–forming reactions. However, reductive elimination reactions from Pd(II) center to form C–O, C–N, or C–F bonds are typically sluggish.

One strategy for promoting otherwise challenging reductive elimination reactions is to oxidize the metal center using an external chemical oxidant. Unfortunately, these oxidants have drawbacks in that they produce undesired byproducts, have poor atom economy, or are expensive.

Thus, the development of novel oxidation systems represents a central challenge in the field of oxidative Pd(II)-catalyzed C–H functionalization. 

MEI's group from Shanghai Institute of Organic Chemistry of the Chinese Academy of Sciences has successfully developed Pd(II)-catalyzed C(sp3)–H functionalization reactions via electrochemical oxidation in JACS.

This catalytic system utilizes electric current to oxidize Pd(II) species to yield high-valent PdIII or PdIV species in the presence of the spectator counteranion, which is then incorporated into the product through reductive elimination.

This catalytic system offers several advantages over traditional methods: 1) it obviates the use of dangerous and toxic reagents; 2) it results in better chemo-selectivity owing to controllable electrolysis; 3) it provides unique platform for mechanistic study. 

This work was financially supported by the Strategic Priority Research Program of the Chinese Academy of Sciences, “1000-Youth Talents Plan”, National Science Foundation (NSF) of China, and Shanghai Science and Technology Committee (S&TCSM). 

 

Palladium-catalyzed C(sp3)-H oxygenation via electrochemical oxidation (Image by MEI)

Attachment:

(Editor: ZHANG Nannan)

Contact

Related Articles

carbon nanotubes; functionalization; carboxyl group; oxygen reduction reaction; biomass conversion

Discovering the Role of Carboxyl Group in Carbon Nanomaterials Catalyzed Reactions

Apr 14, 2015

A cooperation of ZHANG Jian's group and ZHANG Yajie's group from Ningbo Institute of Materials Technology and Engineering of the Chinese Academy of Sciences made a new progress in carbon catalyzed reaction mechanism. They found a pivotal role of carboxyl group on the surf...

2D atomic crystals;Intrinsic pattern;functionalization

New Method to Construct Intrinsically Patterned 2D Materials for Selective Functionalization

Jul 12, 2017

Recently, Prof. GAO Hongjun's group from Institute of Physics of the Chinese Academy of Sciences reported the growth of a family of 2D atomic crystals that are intrinsically patterned and demonstrated that these materials can serve as templates for selective self-assembly...

Contact Us

Copyright © 2002 - 2017 Chinese Academy of Sciences