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Pd II Complexes with N ‐(Diadamantylphosphanyl)diaminocarbene and Related Ligands: Synthesis and Catalytic Applications in Intermolecular Alkyne Hydroaminations
Author(s) -
Marchenko Anatoliy,
Koidan Georgyi,
Hurieva Anastasiya,
Kostyuk Aleksandr,
Franco Dario,
Baron Marco,
Biffis Andrea
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201701342
Subject(s) - carbene , chemistry , hydroamination , alkyne , transition metal carbene complex , intermolecular force , catalysis , ligand (biochemistry) , medicinal chemistry , stereochemistry , molecule , organic chemistry , biochemistry , receptor
A new N ‐diadamantylphosphanyldiaminocarbene 5 is prepared, isolated, and characterized. The carbene appears to be much more stable than previously reported di‐ tert ‐butyl congeners. The molecular structure of the carbene is determined by X‐ray diffraction analysis. A new (diisopropylamino)(diadamantylphosphanyl)carbene 8 is also prepared in situ, but not isolated, since in this case, the adamantyl groups do not render the carbene more stable, with respect to previously known carbenes with di‐ tert ‐butyl substitution. Carbene 8 reacts in situ with phenylazide to give iminophosphane 9 , which is also accessible from carbene 5 upon rearrangement under heating. Stable chelate Pd II complexes are synthesized using both carbene 5 and iminophosphane 9 as ligands. The complex with ligand 9 displays very promising catalytic performance in the intermolecular hydroamination of alkynes with primary arylamines.