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Evaluation of the Electronic Properties of a Carbodiphosphorane through Gold Catalysis
Author(s) -
ElHellani Ahmad,
Bour Christophe,
Gandon Vincent
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100287
Subject(s) - chemistry , triphenylphosphine , divalent , catalysis , tris , medicinal chemistry , carbon fibers , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , materials science , composite number , composite material
Carbodiphosphoranes [C(PR 3 ) 2 ] are divalent carbon(0) derivatives which can be used as ligands to form either M←C(PR 3 ) 2 or (M) 2 ← C(PR 3 ) 2 species. They were computationally predicted to be even stronger electron donors than N‐heterocyclic carbenes. We have introduced hexaphenylcarbodiphosphorane [C(PPh 3 ) 2 ] for the first time in gold catalysis in order to validate this prediction by experimentation. Its mono‐ and digold complexes were compared to tris(2,4‐di‐ tert ‐butylphenyl) phosphite, triphenylphosphine, and 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene in representative gold(I)‐catalyzed transformations. The advantages and limitations of these ligands are discussed.