Premium
A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat‐Water‐Mediated Cross‐Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
Author(s) -
Ramakrishna Visannagari,
Rani Morla Jhansi,
Reddy Nareddula Dastagiri
Publication year - 2017
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.201701241
Subject(s) - chemistry , aryl , reagent , phosphine , palladium , catalysis , medicinal chemistry , base (topology) , ligand (biochemistry) , coupling reaction , organic chemistry , combinatorial chemistry , mathematical analysis , biochemistry , alkyl , receptor , mathematics
The Suzuki–Miyaura cross‐coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh 3 )Cl 2 ] ( I ) [HL1 = 3‐[(2,6‐diisopropylphenyl)‐1‐imidazolio]‐2‐quinoxalinide] as catalyst and K 2 CO 3 as base in neat water. The synthesis of the heterocycle‐containing biaryls required the addition of 2 mol‐% of a phosphine ligand (PPh 3 or X‐Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle‐containing biaryls, diarylmethanes, and benzophenones in moderate‐to‐excellent yields.