Difluoromethyl phenoxathiinium salt: A new general and versatile difluoromethylating reagent with divergent ·CF2H, CF2H+, and:CF2 reactivities

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(3), P. 953 - 962

Published: Dec. 27, 2023

Language: Английский

---

Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1360 - 1366

Published: Feb. 23, 2024

Comprehensive Summary The conversion of CF 3 ‐alkenes to gem ‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use green and readily available reducing salt mediate these reactions remains be explored. In this work, a concise construction gem‐ difluoroalkenes, which requires neither catalyst nor metal agent, was established. Rongalite, safe inexpensive industrial product, employed as both radical initiator reductant. This procedure compatible with linear cyclic diaryliodonium salts, enabling wide variety substrates (>70 examples). utility approach demonstrated through gram‐scale synthesis efficient late‐stage functionalizations anti‐inflammatory drugs.

Language: Английский

---

Violet-Light-Induced Ring-Opening of Anthranils with Chlorodiazirines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

A violet-light-induced ring-opening of anthranils with chlorodiazirines has been developed. The metal-free protocol provides a rapid and efficient approach to N-(2-carbonylaryl)benzamides in moderate good yields under mild conditions. reaction appears involve α-chlorocarbenes, which trigger the anthranils.

Language: Английский

---

Highly stereo- and enantio-selective synthesis of spiro- cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110923 - 110923

Published: Feb. 1, 2025

Language: Английский

---

Stereoselective Palladium-Catalyzed C–F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki–Heck Reaction

Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6217 - 6221

Published: Aug. 16, 2023

A highly diastereoselective Pd(0)-catalyzed Mizoroki-Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C-F bond functionalization with organometallic reagents, this takes place between two different alkenes to achieve a formal and C-H cross-coupling via distinct pathway. Monofluorinated 1,3-diene products can be synthesized control the geometry each alkene good functional group tolerability.

Language: Английский

---

Taming of Furfurylidenes by Chiral Bismuth‐Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1‐Disubstituted (Trifluoromethyl)cyclopropanes

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: Sept. 12, 2023

Although 2-furyl-carbenes (furfurylidenes) are prone to instantaneous electrocyclic ring opening, chiral [BiRh]-paddlewheel complexes empowered by London dispersion allow (trifluoromethyl)furfurylidene metal be generated from a bench-stable triftosylhydrazone precursor. These reactive intermediates engage in asymmetric [2+1] cycloadditions and hence open entry into valuable trifluoromethylated cyclopropane or -cyclopropene derivatives optically active form, which important building blocks for medicinal chemistry but difficult make otherwise.

Language: Английский

---

Photoredox Catalyzed Synthesis of gem-Difluoroalkenes and Monofluorinated Cyclooctenes via 1,5-HAT Process

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4548 - 4553

Published: May 17, 2024

gem-Difluoroalkenes and monofluorinated cycloalkenes have emerged as basic structural units in a variety of bioactive molecules natural products. Thus, developing straightforward efficient methods for synthesizing fluorinated alkene compounds is considerable significance. Herein, we disclose visible-light-induced defluorination 2-trifluoromethyl-1-alkene via 1,5-HAT process using N-alkoxyphtalimides both radical precursor potential nucleophile. The mild stepwise reaction leads to structurally diverse gem-difluoroalkenes cyclooctenes with high efficiency, respectively.

Language: Английский

---

Switchable Divergent Electrochemical Hydrodehalogenation of gem-Dihalocyclopropanes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16929 - 16935

Published: Oct. 29, 2024

A comprehensive and effective electrochemical methodology is introduced for the diverse hydrodechlorination of

Language: Английский

---

Taming of Furfurylidenes by Chiral Bismuth‐Rhodium Paddlewheel Catalysts. Preparation and Functionalization of Optically Active 1,1‐Disubstituted (Trifluoromethyl)cyclopropanes

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(44)

Published: Sept. 12, 2023

Abstract Although 2‐furyl‐carbenes (furfurylidenes) are prone to instantaneous electrocyclic ring opening, chiral [BiRh]‐paddlewheel complexes empowered by London dispersion allow (trifluoromethyl)furfurylidene metal be generated from a bench‐stable triftosylhydrazone precursor. These reactive intermediates engage in asymmetric [2+1] cycloadditions and hence open entry into valuable trifluoromethylated cyclopropane or ‐cyclopropene derivatives optically active form, which important building blocks for medicinal chemistry but difficult make otherwise.

Language: Английский

---