Synthesis of Pd phosphine-imine complexes and their reactivity with base

Authors

Kyle M.K. Jackman, The University of Western Ontario
Amanda A. Fogh, The University of Western Ontario
James M. Stubbs, The University of Western Ontario
Johanna M. Blacquiere, The University of Western OntarioFollow

Document Type

Article

Publication Date

2-1-2019

Journal

Journal of Organometallic Chemistry

Volume

880

First Page

56

Last Page

61

URL with Digital Object Identifier

10.1016/j.jorganchem.2018.10.025

Abstract

Two phosphine-imine ligands were synthesized in which the heteroatoms were connected by an ethyl (1a) or a propyl (1b) linker. Both ligands were reacted with PdCl(Me)(COD), which gave the square planar complexes PdCl(Me)(κ2-P,N-1a) (2a) and PdCl(Me)(κ2-P,N-1b) (2b). Both complexes were treated with base in pyridine in an effort to prepare phosphine 1-azaallyl complexes of the type Pd(Me)(κ2-P,N-L)(py). Deprotonation of 2a gave an intractable mixture of products. In contrast, deprotonation of 2b afforded a new product 4b. However, the site of deprotonation was the methylene adjacent to the phosphine rather than Cα to the imine carbon, deprotonation of which would have afforded a 1-azaallyl moiety.