Fowler, JM orcid.org/0000-0001-6710-4021, Britton, E, Pask, CM orcid.org/0000-0002-2241-5069 et al. (2 more authors) (2019) Cyclotriveratrylene-tethered trinuclear palladium(ii)–NHC complexes; reversal of site selectivity in Suzuki–Miyaura reactions. Dalton Transactions, 39. pp. 14687-14695. ISSN 1477-9226
Abstract
The trinuclear complexes [{PdI2(pyCl)}3(L1)] C1 and [{PdI2(pyCl)}3(L2)] C2, where pyCl = 3-chloropyridine, L1 = methyl(cyclotriguaiacylenyl)methylbenzimidazol-2-ylidene and L2 = benzyl(cyclotriguaiacylenyl)methylbenzimidazol-2-ylidene, each feature three palladium N-heterocyclic carbene (NHC) centres tethered onto a host-type cyclotriguaiacylene scaffold. Crystal structures of different solvates of complex C1 reveal different host–guest motifs including intra-cavity binding of dioxane guests concomitant with intramolecular halogen bonding interactions of C1. Mononuclear NHC analogues of C1 and C2, namely [PdI2(pyCl)(L3)] C3 and [PdI2(pyCl)(L4)] C4, where L3 = (3-chloropyridyl)-1-(2-methoxyphenyoxy)methyl-3-methylbenzimidazol-2-ylidene and L4 = (3-chloropyridyl)-1-(2-methoxyphenyoxy)methyl-3-benzylbenzimidazol-2-ylidene, were also synthesised and their crystal structures determined. Complexes C1–C4 are competent catalysts for Suzuki Miyaura cross-coupling, and interestingly exhibit a switch in the normal regioselectivity observed for reactions of 2,4-dibromopyridine with aryl boronic acids, usually C2-selective, yielding C4-arylated product preferentially over C2-arylated product.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019, The Royal Society of Chemistry. This is an author produced version of a journal article published in Dalton Transactions. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Inorganic Chemistry (Leeds) The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Physical Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 17 Sep 2019 12:14 |
Last Modified: | 20 Sep 2020 02:43 |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Identification Number: | 10.1039/C9DT03400E |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:150915 |