Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Matsumura, Takehiko; Niwa, Takashi; Nakada, Masahisa

doi:10.1016/j.tetlet.2012.06.002

Cited by 43 publications

(23 citation statements)

References 39 publications

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“…To demonstrate synthetic utility of the present strategy, we undertook transformations of methylsulfanyl moieties of 3 . By means of 3 mol % of PdCl 2 and 2.1 equivalents of HSiEt 3 , desulfanylative hydrogenation of 3 aa smoothly proceeded to afford 8 aa in excellent yield (Scheme a). Not only hydrogenation, benzofuran 3 dd was applicable to cross‐coupling with an arylzinc reagent.…”

Section: Methodsmentioning

confidence: 99%

Sigmatropic Dearomatization/Defluorination Strategy for C−F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols

et al. 2018

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Facile synthesis of fluorinated benzofurans from polyfluorophenols has been accomplished by means of a sigmatropic dearomatization/defluorination strategy composed of three processes: (1) interrupted Pummerer reaction of ketene dithioacetal monoxides with polyfluorophenols followed by [3,3] sigmatropic rearrangement, (2) Zn-mediated smooth reductive removal of fluoride from the dearomatized intermediate, and (3) acid-promoted cyclization/aromatization. Mechanistic investigations revealed important characteristic reactivity of polyfluorophenols in the present system. Some of the fluorinated benzofuran products were transformed by utilizing the 2-methylsulfanyl moieties.

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Section: Methodsmentioning

confidence: 99%

Sigmatropic Dearomatization/Defluorination Strategy for C−F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols

et al. 2018

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“…[62]. Nakada also found that palladium catalyzes reduction of aryl sulfides with triethylsilane, which accommodates various functional groups (Scheme 24b) [63].…”

Section: Scheme 18 Cross-coupling Of Aryl Sulfides With Azoles Througmentioning

confidence: 99%

C–S Bond Activation

2018

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“…To further demonstrate the utility of thiazoles 3 obtained, we subjected thiazole 3 aa to transformations of the C−SMe bond. Hydrogenative removal of the methylsulfanyl moiety according to Nakada's protocol uneventfully proceeded to afford 2‐methyl‐5‐phenyl‐1,3‐thiazole ( 5 ) in 85% yield. (Scheme a).…”

Section: Methodsmentioning

confidence: 99%

Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction

2019

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Pummerer-based annulation of alkenyl sulfoxides, mainly ketene dithioacetal monoxides (KDMs), with nitriles has been developed. By means of trifluoromethanesulfonic anhydride (Tf 2 O) as an activator, additive Pummerer reaction and subsequent CÀ S-bond-forming cyclization from the nitrilium intermediates furnished the corresponding thiazoles. Moreover, the nitrilium intermediates proved to be interrupted intermolecularly by H 2 O to afford oxazoles instead of thiazoles.

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Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Cited by 43 publications

References 39 publications

Sigmatropic Dearomatization/Defluorination Strategy for C−F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols

Sigmatropic Dearomatization/Defluorination Strategy for C−F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols

C–S Bond Activation

Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction

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