A visible-light-promoted difluoromethylation/cyclization of 2-vinyloxy arylalkynes was developed, providing a variety of bis(difluoromethyl)-substituted benzofurans in moderate to good yields. A plausible mechanism involving difluoromethyl radical cascade cyclization and solvent-promoted ionic addition was proposed. This protocol has the advantages of having mild reaction conditions, simple operation, and good functional group tolerance.
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Visible-Light-Promoted bis(Difluoromethylation)/Cyclization of 2-Vinyloxy Arylalkynes to Prepare Benzofuran Derivatives.
J Org Chem
October 2022
Guangxi Engineering Research Center for Pharmaceutical Molecular Screening and Druggability Evaluation, College of Pharmacy, Guangxi Key Laboratory of Diabetic Systems Medicine, Guilin Medical University, Guilin 541004, People's Republic of China.
A visible-light-promoted difluoromethylation/cyclization of 2-vinyloxy arylalkynes was developed, providing a variety of bis(difluoromethyl)-substituted benzofurans in moderate to good yields. A plausible mechanism involving difluoromethyl radical cascade cyclization and solvent-promoted ionic addition was proposed. This protocol has the advantages of having mild reaction conditions, simple operation, and good functional group tolerance.
View Article and Find Full Text PDFPalladium-Catalyzed Cascade Difluoroalkylation and Phosphinoylation of 2-Vinyloxy Arylalkynes: Selective Synthesis of Difluoroalkyl-Containing Tetrasubstituted Alkenylphosphine Oxides.
J Org Chem
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School of Public Health, Xinxiang Medical University, Xinxiang 453003, China.
A Pd-catalyzed difluoroalkylation/cyclization/phosphinoylation of 2-vinyloxy arylalkynes with ethyl difluoroiodoacetate and diarylphosphine oxides has been successfully developed. This reaction allows the formation of C-CF, C-C, and C-P(O) bonds in one step, providing a straightforward route to difluoroalkyl-containing tetrasubstituted alkenylphosphine oxides with complete stereoselectivities under mild conditions.
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College of Pharmacy, Guilin Medical University, Guilin 541004, People's Republic of China.
A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
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