Vinyl triflates: a mechanistic study on their formation from carbonyl compounds and triflic anhydride

Pyridone skeletons are found in numerous biologically active molecules and pharmaceuticals. 1-(1-Arylvinyl)pyridin-2(1H)-ones are synthetic intermediates derived from the enamide moiety, and only few examples of the synthesis of 1-(1-arylvinyl)-2-pyridones have been reported. In this work, a simple and efficient procedure for the synthesis of N-vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by base treatment is described. Various ketones with electron-donating or -withdrawing groups at the benzene rings can be used in this reaction. A preliminary mechanistic study indicates that it is not very likely that both vinyl triflates and vinyl cations play major roles as intermediates in this transformation. The thus obtained pyridones can be subsequently transformed via C–H arylation and radical alkylation reactions.

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Computational Mechanistic Study of Thionation of Carbonyl Compounds with Lawesson’s Reagent

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b01420 ◽

2016 ◽

Vol 81 (17) ◽

pp. 7733-7740 ◽

Cited By ~ 22

Author(s):

L. Legnani ◽

L. Toma ◽

P. Caramella ◽

M. A. Chiacchio ◽

S. Giofrè ◽

...

Keyword(s):

Carbonyl Compounds ◽

Mechanistic Study ◽

Lawesson’S Reagent ◽

Lawesson's Reagent

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Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility

Journal of Organometallic Chemistry ◽

10.1016/s0022-328x(03)00611-9 ◽

2003 ◽

Vol 687 (2) ◽

pp. 284-290 ◽

Cited By ~ 33

Author(s):

Tatsuo Ishiyama ◽

Jun Takagi ◽

Akihiro Kamon ◽

Norio Miyaura

Keyword(s):

Carbonyl Group ◽

Carbonyl Compounds ◽

Coupling Reaction ◽

Cross Coupling ◽

Efficient Synthesis ◽

Cross Coupling Reaction ◽

Synthetic Utility ◽

Palladium Catalyzed ◽

Vinyl Triflates

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Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates β-Substituted by a Carbonyl Group: Efficient Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds and Their Synthetic Utility.

ChemInform ◽

10.1002/chin.200415159 ◽

2004 ◽

Vol 35 (15) ◽

Author(s):

Tatsuo Ishiyama ◽

Jun Takagi ◽

Akihiro Kamon ◽

Norio Miyaura

Keyword(s):

Carbonyl Group ◽

Carbonyl Compounds ◽

Coupling Reaction ◽

Cross Coupling ◽

Efficient Synthesis ◽

Cross Coupling Reaction ◽

Synthetic Utility ◽

Palladium Catalyzed ◽

Vinyl Triflates

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Synthesis of 1-(1-Arylvinyl)pyridin-2(1H)-ones from Ketones and 2-Fluoropyridine

10.26434/chemrxiv.14167283 ◽

2021 ◽

Author(s):

Takuji Kawamoto ◽

shunya ikeda ◽

Akio Kamimura

Keyword(s):

Biologically Active ◽

Mechanistic Study ◽

Efficient Procedure ◽

Benzene Rings ◽

Synthetic Intermediates ◽

Alkylation Reactions ◽

Vinyl Triflates

Pyridone skeletons are found in numerous biologically active molecules and pharmaceuticals. 1-(1-Arylvinyl)pyridin-2(1H)-ones are synthetic intermediates derived from the enamide moiety, and only few examples of the synthesis of 1-(1-arylvinyl)-2-pyridones have been reported. In this work, a simple and efficient procedure for the synthesis of N-vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by base treatment is described. Various ketones with electron-donating or -withdrawing groups at the benzene rings can be used in this reaction. A preliminary mechanistic study indicates that it is not very likely that both vinyl triflates and vinyl cations play major roles as intermediates in this transformation. The thus obtained pyridones can be subsequently transformed via C–H arylation and radical alkylation reactions.

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