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Accessing chelating extended linker bis(NHC) palladium(II) complexes: sterically triggered divergent reaction pathways

Wierenga, TS, Vanston, CR, Ariafard, A ORCID: 0000-0003-2383-6380, Gardiner, MG ORCID: 0000-0001-6373-4253 and Ho, CC ORCID: 0000-0002-7555-0635 2019 , 'Accessing chelating extended linker bis(NHC) palladium(II) complexes: sterically triggered divergent reaction pathways' , Organometallics, vol. 38 , pp. 3032-3038 , doi: 10.1021/acs.organomet.9b00356.

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Abstract

We have demonstrated the profound effect that the N-substituent steric bulk of ethylene-linked bis(N-heterocyclic carbene) (bis(NHC)) species has on the mechanism of their formation via Pd(OAc)2-assisted deprotometalations. The binding mode of an ethylene-linked bis(NHC) ligand is chelating when it bears N-2,4-Me2C6H3 substituents but forms a mono(NHC) with a pendant imidazolium group for N-2,6-iPr2C6H3. An N-mesityl-substituted bis(NHC), with steric bulk intermediate between the two aforementioned substituents, generates a mixture of two chelating homoleptic normal/normal and heteroleptic normal/abnormal bis(NHC) complexes, as predicted by DFT calculations. Interestingly, the latter was seen to undergo facile reductive elimination, affording a novel tricyclic monodentate NHC ligand.

Item Type: Article
Authors/Creators:Wierenga, TS and Vanston, CR and Ariafard, A and Gardiner, MG and Ho, CC
Keywords: palladium, carbene, NHC, DFT
Journal or Publication Title: Organometallics
Publisher: Amer Chemical Soc
ISSN: 0276-7333
DOI / ID Number: 10.1021/acs.organomet.9b00356
Copyright Information:

Copyright 2019 American Chemical Society

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