Premium
Alkoxydiaminophosphine Ligands as Surrogates of NHCs in Copper Catalysis
Author(s) -
Pizarro Juan Diego,
Molina Francisco,
Fructos Manuel R.,
Pérez Pedro J.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001517
Subject(s) - nitrene , carbene , chemistry , substituent , phosphine , catalysis , copper , combinatorial chemistry , yield (engineering) , polymer chemistry , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , materials science , metallurgy
A family of phosphine ligands containing a five‐membered ring similar to the popular N‐heterocyclic carbene ligands and an alkoxy third substituent has been developed. These alkoxydiaminophosphine ligands (ADAP) can be generated in one pot and reacted with a copper(I) source leading to the high yield isolation of complexes [(ADAP)CuX] 2 (X=Cl, Br). The dinuclear nature of these compounds has been established by means of X‐ray studies and DOSY experiments. A screening of the catalytic properties of these complexes toward carbene‐transfer reactions from diazocompounds to C−H bonds (alkane, arene), olefins or N−H bonds, as well as in CuAAC or nitrene transfer reactions have shown a performance at least similar, if not better, than their (NHC)CuCl analogues, opening a new window in copper catalysis with these readily tunable ADAP ligands.