Palladacycle versus coordination complex of palladium(II) with a bulky organophosphorus (P,N) ligand: Application in catalysis of allylation of aldehydes

Palladacyclic complex 1 [Pd(L1)Cl] [L1: anthracene–9-yl–CH = N(CH2)2–PPh2 behaving as (P, N, C−) ligand] has been prepared, and characterized using multi-nuclei NMR spectroscopic, high resolution mass spectrometric (HRMS) and single-crystal X-ray diffraction (SC-XRD) techniques. This palladacycle 1...

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Bibliographic Details
Main Authors: Preeti Oswal, Aayushi Arora, Anurag Bahuguna, Suraj Purohit, Khushi Joshi, Pankaj Sharma, Arun Kumar
Format: Article
Language:English
Published: Elsevier 2023-01-01
Series:Results in Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715622004027
Description
Summary:Palladacyclic complex 1 [Pd(L1)Cl] [L1: anthracene–9-yl–CH = N(CH2)2–PPh2 behaving as (P, N, C−) ligand] has been prepared, and characterized using multi-nuclei NMR spectroscopic, high resolution mass spectrometric (HRMS) and single-crystal X-ray diffraction (SC-XRD) techniques. This palladacycle 1 and the 2 [i.e., Pd(L1)Cl2, a square planar Pd(II) complex of the same ligand] have anthracene core, imine functionality and P,N donors. Both the 1 and 2 have been explored as potential catalysts for allylation of aldehydes with allyltributylstannnane. Both the complexes show good efficiency towards this CC coupling reaction. Various aldehydes such as 4–bromobenzaldehyde, 4–chlorobenzaldehyde, 2–bromobenzaldehyde, 2–chlorobenzaldehyde, 4–methoxybenzaldehyde, 4–methylbenzal dehyde, 4–nitrobenzaldehyde pyridine–2–carboxaldehyde and furfural have been explored for this reaction. Effect of presence of Pd–C bond is noticed on the catalytic performance. The palladacyclic complex 1 is more efficient than coordination complex 2 as the Pd-C bond of metallacyclic complex increases the rate of dissociation of Pd-Cl bond and therefore helping in easy participation and increased efficiency of complex 1 in catalysis.
ISSN:2211-7156