The Multifaceted Chemistry of [2.2]Paracyclophane‐Based Thioethers with Palladium(II) Complexes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2024

The Multifaceted Chemistry of [2.2]Paracyclophane‐Based Thioethers with Palladium(II) Complexes

Résumé

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).

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Chimie
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Dates et versions

hal-04593248 , version 1 (29-05-2024)

Identifiants

Citer

Damien Deschamps, Houda Gazzeh, Alice Bonciani, Christopher Richards, Annie-Claude Gaumont, et al.. The Multifaceted Chemistry of [2.2]Paracyclophane‐Based Thioethers with Palladium(II) Complexes. European Journal of Organic Chemistry, 2024, ⟨10.1002/ejoc.202301181⟩. ⟨hal-04593248⟩
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