Catalyst‐Free, Radical Tri‐ and Difluoromethylation of Isocyanides and N‐Arylacrylamides Using Rotating Magnetic Field and Metal Rods

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Comprehensive Summary The pursuit of sustainable and environmentally benign synthetic methods continues to challenge organic chemists. Herein, we introduce a magnetoredox system for tri‐ difluoromethylation isocyanides N ‐arylacrylamides using rotating magnetic field steel rods. This approach enables facile synthesis functionalized phenanthridines oxindoles without the need catalysts additives under mild conditions. Such potentially represents an attractive strategy selective formation bonds through multifaceted regulation intensity, frequency, rod size.

Language: Английский

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Electrochemical Synthesis of Trifluoromethylated Oxazoles: Aminotrifluoromethylation of Alkynes/in‐situ Cyclization

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(16), P. 3450 - 3454

Published: May 31, 2024

Abstract We report the development of a four‐component electrochemical method for synthesis CF 3 ‐oxazoles, utilizing alkynes and NaSO 2 in MeCN. The leverages simplicity mildness reaction conditions, despite inherent complexity four distinct components through aminotrifluoromethylation alkyne followed by in‐situ cyclization. Notably, addition to MeCN solvent, presence residual water mixture also contributed as coupling partner. involves sequence controlled oxidation steps under constant potential with graphite electrodes, facilitated mediator TMEDA, highlighting precision achievable electrochemistry.

Language: Английский

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New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp³)–F Bond Cleavage

JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 466 - 485

Published: Feb. 7, 2025

Fluorinated molecules are of paramount importance because their unique properties. As a result, the search for innovative approaches to synthesis this class compounds has been relentless over years. Among these, combination photocatalysis and organofluorine chemistry turned out be an effective partnership access unattainable fluorinated molecules. This Perspective provides overview recent advances in synthesizing via organophotoredox-catalyzed defluorination process from trifluoromethylated compounds. It encompasses preparation difluoromethylated (hetero)arenes, amides, esters as well gem-difluoroalkene derivatives using C(sp3)–F bond activation or β-fragmentation. will highlight remaining challenges discuss future research opportunities.

Language: Английский

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Rhodium- and Iridium-Catalyzed (Enantioselective) Fluoroamidation of gem-Difluoroalkenes via Chelation Assistance

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6555 - 6562

Published: April 7, 2025

Language: Английский

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Photoinduced Copper‐Mediated Difluoroalkylation of Arylsulfonium Salts with XCF₂COR

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

Abstract Photoredox fluoroalkylation has emerged as a powerful method and have unlocked new possibilities in organic chemistry. In this work, the green‐light‐induced copper‐mediated difluoroalkylation of arylsulfonium salts with different XCF 2 COR reagents is described. The reaction proceeded smoothly at ambient temperature under mild conditions allowed formation variety difluoroalkylated arenes good yields. photocatalyst, visible‐light, Cu(I) salt played synergetic role reduction to respective radical intermediates. This metallophotoredox protocol was applicable late‐stage multifunctionalized bioactive molecules, offering opportunities discovery medicinal agents. transformation showed advantages mildness, simple operation, functional group tolerance, wide range substrates, excellent regioselectivity, which provided an interesting alternative other reactions terms structural diversity, selectivity, availability by application platforms.

Language: Английский

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Electrochemical Trifluoromethylation of Alkynes: The Unique Role of DMSO as a Masking Auxiliary

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical trifluoromethylation method for terminal alkynes has been developed, facilitating the synthesis of CF 3 -alkynes with DMSO as a masking auxiliary.

Language: Английский

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