Premium
A Robust and Efficient Catalyst Possessing an Electron‐Deficient Ligand for the Palladium‐Catalyzed Direct Arylation of Heteroarenes
Author(s) -
Jakab Alexandra,
Dalicsek Zoltán,
Soós Tibor
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402586
Subject(s) - chemistry , palladium , catalysis , pivalic acid , aryl , regioselectivity , combinatorial chemistry , triphenylphosphine , cyanation , ligand (biochemistry) , phosphine , metalation , trifluoromethyl , medicinal chemistry , organic chemistry , photochemistry , biochemistry , alkyl , receptor
The exploration of the direct arylation capacity of a unique, thermally stable, and air‐stable Pd 0 –phosphine catalyst is reported. Besides decisively contributing to catalyst robustness, the electron‐deficient trifluoromethyl‐substituted triphenylphosphine ligands make the palladium center more electron‐deficient and accelerate the direct arylation step. The combination of only 0.5–2 mol‐% of the catalyst and a substoichiometric quantity of pivalic acid generates an efficient system to promote biaryl‐forming reactions of a broad range of electronically varied hetarenes and aryl bromides. The observed regioselective arylations suggest that a concerted metalation–deprotonation pathway is involved in the C–H activation step.