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Stable Di‐ and Tri‐coordinated Carbon(II) Supported by an Electron‐Rich β‐Diketiminate Ligand
Author(s) -
Regnier Vianney,
Planet Yoan,
Moore Curtis E.,
Pecaut Jacques,
Philouze Christian,
Martin David
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610798
Subject(s) - electrophile , reactivity (psychology) , adduct , chemistry , ligand (biochemistry) , carbon fibers , stereochemistry , medicinal chemistry , crystallography , combinatorial chemistry , organic chemistry , materials science , catalysis , biochemistry , medicine , alternative medicine , receptor , pathology , composite number , composite material
Abstract Complexes of the ubiquitous β‐diketiminates (NacNac) ligands have been reported with most elements of the periodic table, including Group 14 Si, Ge, Sn, and Pb. The striking absence of carbon representatives has been attributed to the extreme electrophilicity of the putative C‐NacNac adducts. An electron enriched 2,4‐(dimethylamino)diketiminato backbone is described, which allowed for the synthesis and isolation of such stable pyrimidin‐1,3‐diium and pyrimidinium‐2‐ylidene salts. Structural and preliminary reactivity studies are reported, including an air‐stable gold complex. An unforeseen original class of stable N‐heterocyclic carbenes and, more generally, the potential of electron‐rich NacNac patterns for taming highly electrophilic centers are showcased.