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Me CAAC=N − : A Cyclic (Alkyl)(Amino)Carbene Imino Ligand
Author(s) -
Goettel James T.,
Gao Haopeng,
Dotzauer Simon,
Braunschweig Holger
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.201904715
Subject(s) - carbene , ligand (biochemistry) , alkyl , chemistry , stereochemistry , medicinal chemistry , physics , organic chemistry , receptor , biochemistry , catalysis
Abstract A cyclic (alkyl)(amino)carbene (CAAC) has been shown to react with a covalent azide similar to the Staudinger reaction. The reaction of Me CAAC with trimethylsilyl azide afforded the N‐silylated 2‐iminopyrrolidine ( Me CAAC=NSiMe 3 ), which was fully characterized. This compound undergoes hydrolysis to afford the 2‐iminopyrrolidine and trimethylsiloxane which co‐crystallize as a hydrogen‐bonded adduct. The N‐silylated 2‐iminopyrrolidine was used to transfer the novel pyrrolidine‐2‐iminato ligand onto both main‐group and transition‐metal centers. The reaction of the tetrabromodiborane bis(dimethyl sulfide) adduct with two equivalents of Me CAAC=NSiMe 3 afforded the disubstituted diborane. The reaction of Me CAAC=NSiMe 3 with TiCl 4 and CpTiCl 3 afforded Me CAAC=NTiCl 3 and Me CAAC=NTiCl 2 Cp, respectively.