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- W2014736311 abstract "The reaction of [Pd(C6F5)Br(NCMe)2] with the allylic sulfides R1SCH2CHCH2 (R1 = −CH2CHCH2, Me), n-BuSCHMeCHCH2, and n-BuSCH2CHCHMe results in insertion of the double bond into the Pd−C6F5 bond and β-SR elimination (C−S cleavage) to give the corresponding (pentafluorophenyl)alkenes and a palladium thiolate. With alkenyl sulfides of longer carbon chains RS(CH2)nCHCH2 (R = n-Bu, Ph; n = 2, 3) five-membered (n = 2, 13, 14) or six-membered (n = 3, 16, 17) σ-yl-κS-palladacycles were obtained. The six-membered derivatives isomerize to the corresponding five-membered palladacycles (18, 19) by one-step Pd-migration (Pd−H elimination−readdition). Inversion of the coordinated sulfur is observed in these derivatives, and the dynamic process has been studied for the monomeric complexes [(σ-κS-(Rthio)alkyl)Pd(acac)] (13b, 14b, 18b, 19b). ΔG⧧Tc values show that the S-inversion is easier for the Ph-substituted than for the n-Bu-substituted complexes. The decomposition of the σ-yl-κS palladacycles occurs through Pd-migration and, when Pd and S are placed three bonds apart in the chain, β-SR elimination; this is the same process observed in the reaction of [Pd(C6F5)Br(NCMe)2] with allylic sulfides. Double bond isomerization of the (pentaflurophenyl)alkene products formed in the decomposition reactions is observed, catalyzed by “Pd−H” intermediates. Double pentafluorophenyl arylation is also observed in some cases." @default.
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- W2014736311 title "Insertion of Alkenyl Sulfides into a Palladium−Aryl Bond. 2. Stabilization of σ-yl-κ<i>S</i> Chelates and Decomposition Reactions through C−S Cleavage" @default.
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- W2014736311 doi "https://doi.org/10.1021/om9604076" @default.
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