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A Copper‐Catalyzed Variant of the Michaelis–Arbuzov Reaction
Author(s) -
Ballester Jorge,
Gatignol Jérémie,
Schmidt Guntram,
Alayrac Carole,
Gaumont AnnieClaude,
Taillefer Marc
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201301029
Subject(s) - aryl , chemistry , phosphine , catalysis , nucleophile , copper , palladium , organic chemistry , ligand (biochemistry) , homogeneous catalysis , combinatorial chemistry , nickel , alkyl , biochemistry , receptor
As part of our studies on copper‐catalyzed arylation of nucleophiles, we report on Michaelis–Arbuzov reactions with a novel catalytic system, featuring a copper(I) salt as precatalyst without any additional ligand. This procedure is an interesting alternative to the use of expensive and toxic transition metals (nickel, palladium) traditionally used as catalysts in Michaelis–Arbuzov reactions. Our approach allows the synthesis from triethylphosphite, diethyl aryl phosphonite, and diaryl ethylphosphinite of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides, respectively. These families of compounds are essential owing to their respective importance in bioorganic and medical chemistry, their applicability as flame retardants, and their usability in coordination chemistry and catalysis.