A Radical Process towards the Development of Transition-Metal-Free Aromatic CarbonCarbon Bond-Forming Reactions

Transition‐metal‐free cross‐coupling reactions have been a hot topic in recent years. With the aid of a radical initiator, a number of unactivated arene CH bonds can be directly arylated/functionalized by using aryl halides through homolytic aromatic substitution. Commercially available or speciall...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2013-11, Vol.19 (47), p.15802-15814
Main Authors: Chan, Tek Long, Wu, Yinuo, Choy, Pui Ying, Kwong, Fuk Yee
Format: Article
Language:English
Subjects:
Amino Alcohols - chemistry
Aromatic compounds
biaryl
Bonding
Carbon - chemistry
Catalysis
Catalysts
cross-coupling
CC bond formation
Diamines - chemistry
Diols
Free Radicals - chemistry
homolytic aromatic substitution
Impurities
radical reactions
Radicals
Transition Elements - chemistry
Transition metals
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Transition‐metal‐free cross‐coupling reactions have been a hot topic in recent years. With the aid of a radical initiator, a number of unactivated arene CH bonds can be directly arylated/functionalized by using aryl halides through homolytic aromatic substitution. Commercially available or specially designed promoters (e.g. diamines, diols, and amino alcohols) have been used to make this synthetically attractive method viable. This protocol offers an inexpensive, yet efficient route to aromatic CC bond formations since transition metal catalysts and impurities can be avoided by using this reaction system. In this article, we focus on the significance of the reaction conditions (e.g. bases and promoters), which allow this type of reaction to proceed smoothly. Substrate scope limitations and challenges, as well as mechanistic discussion are also included. No need for transition metals anymore: Joining two aromatic fragments by using an attractive transition‐metal‐free homolytic aromatic substitution pathway provides an efficient route to aromatic CC bond formation, since transition metal catalysts and impurities can be avoided by using this reaction system (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201301583