The multifaceted chemistry of [2.2]paracyclophane-based thioethers with palladium(II) complexes

Deschamps, Damien; Gazzeh, Houda; Bonciani, Alice; Richards, Christopher J.; Gaumont, Annie-Claude; Perrio, Stéphane

doi:10.1002/ejoc.202301181

The multifaceted chemistry of [2.2]paracyclophane-based thioethers with palladium(II) complexes

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Deschamps, Damien, Gazzeh, Houda, Bonciani, Alice, Richards, Christopher J., Gaumont, Annie-Claude and Perrio, Stéphane (2024) The multifaceted chemistry of [2.2]paracyclophane-based thioethers with palladium(II) complexes. European Journal of Organic Chemistry, 27 (8). ISSN 1434-193X

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Abstract

The reactions of planar chiral ([2.2]paracyclophan-4-yl)methyl thioethers ([2.2]PCP-CH2-SR) with various palladium(II) sources (PdL2) were studied. Unexpectedly, with most of the sulfur substrates investigated (SR=Ph, 2-pyridyl, Me, n-dodecyl), and independently of the PdL2 salt employed (L=TFA, OAc, OPiv, Cl, Br), loss of the SR sulfanyl unit, along with incorporation of one palladium L ligand to the lateral benzylic position of the [2.2]PCP core, has been observed. In contrast, the precursor featuring a t-butylsulfanyl group (R=t-Bu) exhibited a distinct reactivity. An ortho C(sp2)−H activation took place, and allowed the formation of a [2.2]paracyclophane-based SC-palladacycle, in an efficient and highly diastereoselective manner (83 % yield, single diastereoisomer).

Item Type:	Article
Additional Information:	Data Availability Statement: The data that support the findings of this study are available in the supplementary material of this article.
Uncontrolled Keywords:	sulfur,palladium,[2.2]paracyclophane,c−h activation,palladacycle,ligand exchange,functionalization,functionalization,physical and theoretical chemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1606
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	28 Oct 2025 10:31
Last Modified:	03 Nov 2025 17:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/100810
DOI:	10.1002/ejoc.202301181

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