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Facile Synthesis of Phosphaamidines and Phosphaamidinates using Nitrilium Ions as an Imine Synthon
Author(s) -
van Dijk Tom,
Burck Sebastian,
Rong Mark K.,
Rosenthal Amos J.,
Nieger Martin,
Slootweg J. Chris,
Lammertsma Koop
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405027
Subject(s) - synthon , chemistry , imine , tetrahydrothiophene , denticity , lithium (medication) , ligand (biochemistry) , trimer , ion , combinatorial chemistry , stereochemistry , medicinal chemistry , crystal structure , dimer , crystallography , organic chemistry , catalysis , medicine , biochemistry , receptor , endocrinology
Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of a novel class of 1,3‐P,N ligands as demonstrated for the reaction with primary phosphanes. This procedure allows variation of all substituents. X‐ray crystal structures are reported for nitrilium ions, phosphaamidines, and three phosphaamidinate complexes. The lithium phosphaamidinate is N coordinated and its reaction with [AuCl(tht)] (tht=tetrahydrothiophene) gives a unique P‐bridged gold trimer, while a P,N‐bidentate complex results from [{RhCl(cod)} 2 ]. The nitrilium ion methodology allows extension of the 1,3‐P,N motive to bis(imino)phosphanes, which are the neutral phosphorus analogues of the valuable β‐diketiminate ligand.