Facile double O-difluoromethylations of diphenols with TMSCF2Br DOI
Fanjing Kong,

Rongyi Zhang,

Xiu Wang

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 152, P. 155335 - 155335

Published: Oct. 18, 2024

Language: Английский

Photodriven Radical Perfluoroalkylation–Thiolation of Unactivated Alkenes Enabled by Electron Donor–Acceptor Complex DOI

Lixin Liu,

Qian Wang, Yuanhua Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2271 - 2275

Published: March 8, 2024

A clean and direct three-component radical 1,2-difunctionalization of various alkenes with perfluoroalkyl iodides thiosulfonates enabled by the electron donor–acceptor complex has been developed under light illumination at room temperature. The approach offers a convenient environmentally friendly route for simultaneous incorporation Csp3–Rf Csp3–S bonds, affording valuable polyfunctionalized alkane derivatives containing fluorine sulfur in satisfactory yields. Consequently, this methodology holds significant value practicality field organic synthesis.

Language: Английский

Citations

7

Controllable Fluorocarbon Chain Elongation: TMSCF2Br-Enabled Trifluorovinylation and Pentafluorocyclopropylation of Aldehydes DOI
An Liu, Xianghong Zhang, Feng Zhao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(3), P. 1806 - 1812

Published: Jan. 9, 2024

Controllable fluorocarbon chain elongation (CFCE) is a promising yet underdeveloped strategy for the well-defined synthesis of structurally novel polyfluorinated compounds. Herein, direct and efficient trifluorovinylation pentafluorocyclopropylation aldehydes are described by using TMSCF

Language: Английский

Citations

6

Truce-smiles rearrangement mediated by ligand-to-iron charge transfer DOI Creative Commons

Fuyang Yue,

Ming‐Xing Li, Kangkang Yang

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0

Advances in the Synthetic Utility of Difluorocarbene Generated from TMSCF3 (Ruppert‐Prakash Reagent) and Its Derivatives DOI Open Access
Jagadeesh Krishnan,

Kaja Sahib,

Keerthana G. Nair

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Abstract Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries different strategies have been designed for their synthesis. The last two decades witnessed the emergence difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises reactions generated from Ruppert‐Prakash reagent (TMSCF 3 ) its derivatives TMSCF 2 Cl Br. Among various fluorination techniques available, chemistry offers a cost effective procedure, opening avenue large number details developments utility derivatives, till date.

Language: Английский

Citations

0

Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI
Shuai Liu, Jun Zhou, Lu Yu

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

0

Copper difluorocarbene-involved catalytic gem-difluoropropargylation DOI Creative Commons
Xin Zeng,

Shi‐Ping Sun,

Haiyang Zhao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: May 15, 2025

The use of metal for catalytic difluorocarbene transfer reactions has long been hindered by the lack understanding chemistry, despite potential implications medicinal chemistry and advanced materials science. Here, we report a copper-catalyzed reaction via 1,1-migration copper difluorocarbene, in contrast to previous nucleophilic addition pathway. This enables development modular gem-difluoropropargylation using variety simple widely available potassium propiolates, terminal alkynes, allyl/propargyl electrophiles couple opening an avenue precise synthesis organofluorine compounds without tedious synthetic procedures. impact this protocol is demonstrated efficient complex fluorinated skeletons rapid key intermediates pheromone derivatives PGF2 agonists. Mechanistic studies reveal that migratory insertion into C-Cu bond alkynylcopper species step reaction.

Language: Английский

Citations

0

Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters DOI
Xiang Huang,

Dongzhen Xu,

Junyang Liu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(12), P. 109665 - 109665

Published: Feb. 23, 2024

Language: Английский

Citations

3

Palladium-Catalyzed Four-Component Radical Cascade Carbonylation Access to 2,3-Disubstituted Benzofuran Derivatives DOI
Ming Li,

Dong‐Yu Miao,

Fan Gao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

Multicomponent radical tandem reactions have emerged as a crucial technique for synthesizing complex molecules in organic chemistry. In this study, we report palladium-catalyzed four-component difluoroalkylative carbonylation of enynes and ethyl difluoroiodoacetate. This transformation proceeds through multistep sequential reaction that introduces reactive difluoro carbonyl groups while constructing the benzofuran skeleton. Moreover, variety valuable 2,3-disubstituted derivatives were obtained respectable yields with excellent functional group compatibility.

Language: Английский

Citations

2

Photocatalytic Decarboxylative Fluoroalkylation of α,β‐Unsaturated Carboxylic Acids DOI Open Access

xiuling Wang,

Yaxing Wu,

Songlin Xu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract A decarboxylative fluoroalkylation of α,β‐unsaturated acids was developed by the use a dual nickel/photoredox catalysis system. The fluoroalkyl radicals are generated from α‐CF 3 alkyl bromides nickel‐induced single electron transfer (SET) and subsequently intercepted cinnamic acid to forge targeted C−C bonds. wide variety substrates bearing diverse set functional groups were compatible with mild reaction conditions (visible light, room temperature, cheap metal, no strong oxidant or reductant), thus affording trifluoromethyl analogues α‐methylated allylic compounds.

Language: Английский

Citations

2

Three-component approach to modular synthesis of tetra-substituted furans and pyrroles DOI
Pei Zhang,

Wenqing Ti,

Tianfeng Gao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2554 - 2560

Published: Jan. 1, 2024

A three-component one-pot reaction of TMSCF 2 Br, p -QMs and 1,3-dicarbonyl compounds derivatives was developed. series densely functionalized tetra-substituted furans pyrroles were constructed with excellent chemoselectivities.

Language: Английский

Citations

1