Oxidative addition of allyl and propargyl halides on palladium(0) complexes bearing bidentate ligands with quinolinic structure

Canovese, Luciano; Visentin, Fabiano; Biz, Chiara; Scattolin, Thomas; Santo, Claudio; Bertolasi, Valerio

doi:10.1016/j.jorganchem.2015.01.023

Cited by 15 publications

(12 citation statements)

References 72 publications

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“…The ligands 8-(methylthio)quinoline (TMQ), and 8-(tbutylthio)quinoline 10 and complexes 1a and 1e 5j were obtained according to published protocols.…”

Section: Ir Nmr Uv-vis Measurements and Elemental Analysismentioning

confidence: 99%

The unexpected case of reactions of halogens and interhalogens with halide substituted Pd(ii) σ-butadienyl complexes

et al. 2016

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We have experimentally studied and theoretically interpreted the addition under stoichiometric conditions of halogens or interhalogens to σ-butadienyl palladium complexes bearing the heteroditopic thioquinolines as spectator ligands. The observed reactions do not involve the expected extrusion of the butadienyl fragment but rather the unpredictable substitution of the halide coordinated to palladium and in some cases also of that bound to the terminal butadienyl carbon. We have explained this peculiar reactivity with a mechanistic hypothesis based on a sequence of selective processes of oxidative addition and reductive elimination involving Pd(iv) intermediates.

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“…The ligands 8-(methylthio)quinoline (TMQ), and 8-(tbutylthio)quinoline 10 and complexes 1a and 1e 5j were obtained according to published protocols.…”

Section: Ir Nmr Uv-vis Measurements and Elemental Analysismentioning

confidence: 99%

The unexpected case of reactions of halogens and interhalogens with halide substituted Pd(ii) σ-butadienyl complexes

et al. 2016

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“…The ligands DPPQ [11], Me-DPPQ [12], TtBQ and TMQ [5], MeTtBQ [13], Me-TMQ [10], and of the complexes 1, 4 [8] and 2,3 http://dx.doi.org/10.1016/j.poly.2015.07.049 0277-5387/Ó 2015 Elsevier Ltd. All rights reserved. [5] were obtained according to published protocols, whereas the complexes 5 and 6 are newly synthesized compounds.…”

Section: General Considerationsmentioning

confidence: 99%

“…[5] were obtained according to published protocols, whereas the complexes 5 and 6 are newly synthesized compounds.…”

Section: General Considerationsmentioning

confidence: 99%

“…The ligands DPPQ [11], DPPQ-Me [12], TtBQ and TMQ [5], MeTtBQ [13], Me-TMQ [10], and of the complexes 1, 4 [8] and 2, 3 [5] were synthesized according to published procedures. (4); Pd1-N1 = 2.158(3); Pd1-S1 = 2.313(1); Pd1-C14 = 1.986 (3); S1-C6 = 1.779 (4); S1-C10 = 1.887 (4).…”

Section: Synthesis Of the Ligands And Complexesmentioning

confidence: 99%

“…In this respect, we have recently published a paper in which we discussed some aspects of the preferential formation of allenyl or propargyl tautomeric derivatives when propargyl halides react with some dimethylfumarate (dmfu) stabilized Pd(0) complexes bearing thioetheric or diphenyl phosphine quinoline-based ancillary ligands. We were able to isolate the reaction products, resolve the solid state structure of some of them and surmise a plausible mechanism on the basis of some computational and kinetic studies [5].…”

Section: Introductionmentioning

confidence: 99%

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Oxidative addition of organic halides on palladium(0) complexes stabilized by dimethylfumarate and quinoline-based N–P or N–S spectator ligands

et al. 2015

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a b s t r a c tWe have studied the oxidative addition of some organic halides on palladium(0) dimethylfumarate complexes bearing heteroditopic (N-P or N-S) quinoline-based spectator ligands from the experimental and theoretical point of view. We have measured the half-life of some oxidative addition reactions carried out in two different solvents (CD 2 Cl 2 and CD 3 CN). The reactions were studied under mild conditions by NMR and the reactivities of different oxidants towards the complexes under study were compared. The rates of reaction were influenced by the nature of the spectator ligands and the solvent. The thioquinoline derivatives display a higher reactivity than that of the phosphoquinoline complexes and in general the reaction rates are higher in CD 3 CN than in CD 2 Cl 2 , although such a behavior is not always observed. We propose a plausible mechanism for the oxidative reaction in different solvents based on the experimental results and an adequate computational approach. Finally, the solid state structures of two reaction products were resolved and reported.

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One‐Pot Synthesis of 2‐(Alkylsulfanyl)quinolines from Aryl Isothiocyanates and Allenes or Alkynes

Nedolya,

Tarasova,

Artem'ev

et al. 2024

Eur J Org Chem

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In this work, a conceptually novel approach to diversely substituted 2‐(alkylsulfanyl)quinolines is described. The approach includes the assembly of the target molecules from allenic or acetylenic carbanions, aromatic isothiocyanates, and alkylating agents, The process proceeds in a single synthetic operation via the formation and 6π‐electrocyclization of N‐aryl‐1‐aza‐1,3,4‐trienes, R2R3C=C=C(R1)C(SAlk)=NAr, with the participation of the carbon‐carbon double bond of the phenyl group and the azadiene fragment of the azatrienic system.

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Oxidative addition of allyl and propargyl halides on palladium(0) complexes bearing bidentate ligands with quinolinic structure

Cited by 15 publications

References 72 publications

The unexpected case of reactions of halogens and interhalogens with halide substituted Pd(ii) σ-butadienyl complexes

The unexpected case of reactions of halogens and interhalogens with halide substituted Pd(ii) σ-butadienyl complexes

Oxidative addition of organic halides on palladium(0) complexes stabilized by dimethylfumarate and quinoline-based N–P or N–S spectator ligands

One‐Pot Synthesis of 2‐(Alkylsulfanyl)quinolines from Aryl Isothiocyanates and Allenes or Alkynes

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