1.6 Synthesis of Difluoromethylated Compounds DOI
Simin Wu, Hayeon Song, Mingyou Hu

et al.

Published: Jan. 1, 2024

Abstract The difluoromethyl group (CF2H) can function as a lipophilic hydrogen-bond donor, and is regarded bioisostere of functional groups such hydroxy (-OH), thiol (-SH), amino (-NH2). unique physicochemical properties this make difluoromethylation hot topic in the field synthetic organic chemistry, recent decades, various methods have been developed for constructing C(sp3)—CF2H, C(sp2)—CF2H, C(sp) —CF2H, X—CF2H (X = N, O, S, Se, B, P, etc.) bonds. This review summarizes currently available reagents performing reactions, well other approaches installing unit.

Language: Английский

General radical difluoromethylation using difluoroacetic anhydride via photoredox catalysis DOI
Meng He,

Yankai Yang,

Heng Zhang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 2637 - 2646

Published: June 26, 2024

Language: Английский

Citations

2
C–F bond functionalizations via fluorinated carbenes DOI

Yingmei Li,

Jiangbin Luo, Yaojia Jiang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5782 - 5804

Published: Jan. 1, 2023

This feature article summarizes the developments in fluorinated carbene transformations, and their consequent C–F functionalization a cascade platform.

Language: Английский

Citations

5
From intramolecular cyclization to intermolecular hydrolysis: TMSCF2Br-enabled carbonylation of aldehydes/ketones and amines to α-hydroxyamides DOI Creative Commons

An Liu,

Shuo Sun, Qiqiang Xie

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5343 - 5351

Published: Jan. 1, 2023

An unprecedented metal-free multicomponent reaction enables rapid and straightforward access to structurally diverse α-hydroxyamides from carbonyl compounds (aldehydes/ketones), difluorocarbene amines.

Language: Английский

Citations

4
Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis DOI Open Access

Zhi Tu,

Jin‐Sheng Yu, Jian Zhou

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(10), P. 3491 - 3491

Published: Jan. 1, 2023

Bromodifluoromethyl trimethylsilane (TMSCF2Br) has proved to be an important difluoromethyl(alkyl)ation reagent that is widely applied in organic synthesis over the past decade, since it was used as a difluorocarbene precursor 2011.This review aims provide briefly summary for of TMSCF2Br, and introduce recent advances applications TMSCF2Br or trimethylsilyldifluoromethyl radical developing various difluoromethyl(alkyl)ations different kinds substrates.Meanwhile, activation ways possible mechanism, well its advantages disadvantages each kind reactions are detailedly disccussed, which might some references inspiration researchers engaged fluorine chemistry.

Language: Английский

Citations

4
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
Radical Decarboxylation-Initiated SH2′ Reaction of β,β-Difluoroenol Sulfonates: Access to α,α-Difluoroketones DOI

Bingbing Pei,

Jiali Wang,

Jiuyang Ji

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4797 - 4802

Published: May 26, 2024

Reported herein is a novel radical decarboxylation-initiated S

Language: Английский

Citations

1
Halogen-bond-assisted radical remote difunctionalization of bicyclo[1.1.1]butane skeleton DOI
Hui Liu, Zhenda Fu, Xingwei Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Transition-metal-free radical remote difunctionalization of bicyclo[1.1.1]butane skeletons in both two- and three-component fashions is presented.

Language: Английский

Citations

1
Difluorocarbene as a C–F source for the construction of fluorinated benzothiazoles DOI

Wen-Jie Pan,

Yu Jiao,

Weiguo Cao

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 120 - 126

Published: Nov. 13, 2023

Described herein is the use of difluorocarbene as a C–F source for cyclization 2-aminobenzenethiols to provide fluorinated benzothiazoles. A one-step process installs fluorine atom and constructs heterocycle.

Language: Английский

Citations

3
Controllable Double Difluoromethylene Insertions into S−Cu Bonds: (Arylthio)tetrafluoroethylation of Aryl Iodides with TMSCF2Br DOI

Shitao Pan,

Qiqiang Xie, Xiu Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(14)

Published: Feb. 15, 2024

Abstract A new method of constructing “ArSCF 2 CF Cu” from ArSCu and TMSCF Br (TMS=trimethylsilyl) has been developed. The cross‐coupling reactions the obtained with diverse aryl iodides (Ar′I) provide an efficient access to Ar′CF SAr. Mechanistic studies demonstrate that species were generated through controllable double difluoromethylene insertions into ArS−Cu bonds rather than 1,2‐addition tetrafluoroethylene.

Language: Английский

Citations

0
Interaction of Difluorocarbene with the Thiocyanate Anion: Access to a Silicon Reagent Bearing the Isothiocyanate Group DOI
Alexey L. Trifonov, Alexander D. Dilman

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

Published: Nov. 26, 2024

The reaction between (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and potassium thiocyanate providing TMSCF2NCS is described. process involves the interaction of difluorocarbene with nitrogen atom anion. obtained silicon reagent served as a source fluorinated group in N-alkyl imines, affording 2-(difluoromethylthio)-4-fluoroimidazoles.

Language: Английский

Citations

0