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

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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… Click to show full abstract

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.

Keywords: imine complexes; synthesis phosphine; phosphine imine; deprotonation; imine

Journal Title: Journal of Organometallic Chemistry
Year Published: 2019

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