Photocatalytic Three-Component Reductive Coupling Synthesis of gem-Difluorohomoallyl Secondary Amines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

gem-Difluorohomoallyl amines, an important class of gem-difluoroalkenes, are prevalent moieties in many bioactive compounds. However, limited methods suitable for the synthesis this type compound containing secondary amines. Here, we display a photocatalytic multicomponent protocol gem-difluoroalkenes which makes use readily available materials: arylamines, alkyl aldehydes, and α-trifluoromethyl alkenes. Moreover, ketones amines also substrates. Preliminary mechanistic experiments indicate that key α-amino radical was involved, generated from reduction situ-formed imines (or iminium ions) by reduced photocatalyst. Subsequent addition to alkenes β-F elimination deliver desired products.

Language: Английский

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Visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions: simple FeBr3 as a dual-functional catalyst

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6198 - 6204

Published: Jan. 1, 2024

Reported herein is a visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions, with simple FeBr 3 as dual-functional catalyst.

Language: Английский

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Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 25, 2025

p-CF3BnSeCF2Br was developed as a bromodifluoromethylselenonating reagent, which utilized by combining with mCPBA and Tf2O for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via selenolation/lactonization 2-alkynylbenzoates. The transformation postulated to proceed multicomponent reagents system-enabled sequence involving oxidation into its selenium sulfoxide, activation generated sulfoxide electrophilic p-CF3BnSeOCF2Br salt, 2-alkynylbenzoates reactive species isocoumarins.

Language: Английский

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Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4905 - 4911

Published: Jan. 1, 2023

Herein, we have reported a metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes to construct α-trifluoromethylselenolated ketones and trifluoromethylselenolated alkynes.

Language: Английский

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Synthesis of 2-substituted 3-trifluoromethylselenoindoles via a SeCF₃ migration reaction

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3968 - 3973

Published: Jan. 1, 2024

The synthesis of 2-substituted 3-trifluoromethylselenoindoles via a zinc-mediated SeCF 3 migration is reported.

Language: Английский

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Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 15, 2024

Abstract An expedient strategy for the construction of trifluoromethylselenolated spiro[5.5]trienones/spiro[4.5]trienones through a cascade electrophilic trifluoromethylselenolation cyclization and dearomatization has been developed. This sequential process was induced by N ‐trifluoromethylselenophthalimide (Phth‐SeCF 3 ), which an efficient reagent. approach feature mild conditions, broad substrate scope, high functional group tolerance.

Language: Английский

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