A Practical and General Synthesis of Unsymmetrical Terphenyls

A synthetic procedure was developed that enables sequential chemoselective Suzuki−Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2007-09, Vol.72 (20), p.7771-7774
Main Authors: Antelo Miguez, Jose M, Adrio, Luis Angel, Sousa-Pedrares, Antonio, Vila, Jose M, Hii, King Kuok (Mimi)
Format: Article
Language:English
Subjects:
Boronic Acids - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Chlorobenzenes - chemistry
Exact sciences and technology
General and physical chemistry
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Terphenyl Compounds - chemical synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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:A synthetic procedure was developed that enables sequential chemoselective Suzuki−Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo701308b