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

Nickel-catalyzed reductive cross-coupling of difluoromethylated secondary alkyl bromides with organohalides DOI
Bosheng Liu,

Jinxu Dong,

Hongyi Wang

et al.

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

Published: Jan. 1, 2025

We present a highly efficient and versatile nickel-catalyzed protocol for the reductive cross-coupling of unactivated CF2H-substituted electrophiles with wide variety aryl alkenyl halides. This novel approach offers high catalytic reactivity broad functional group compatibility, enabling late-stage fluoroalkylation drug molecules.

Language: Английский

Citations

0
Difluorocarbene-Mediated Trimethylsilylation of Nucleophiles with HCF2N(TMS)2 as a Silylation Reagent DOI

Hao Ruan,

Dong Zhu,

Jingwei Zhao

et al.

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

Published: Feb. 10, 2025

Described herein is the trimethylsilylation of various nucleophiles using a combination HCF3 and NaHMDS. This facile protocol enables rapid construction alkynylsilanes, silyl enol ethers, etc., under mild conditions. Detailed mechanistic studies indicate that trimethylsilicon intermediate formed in situ can be readily attacked by nucleophiles, with activation base NaHMDS difluorocarbene. work first utilizes structure HMDS as silicon source terminal alkynes.

Language: Английский

Citations

0
Recent Advances in Transition-Metal Catalyzed C—H Bond Activation for the Synthesis of C(sp3)-Fluoroalkyl Compounds DOI
Manman Wang, Wenhui Xi, Hao Wu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 516 - 516

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photoredox-Catalyzed Direct C(sp2)–H Difluoromethylation of Hydrazones with Difluoromethyltriphenylphosphonium Salt via Aminyl Radical/Polar Crossover DOI

Xiao‐Di Wu,

Wang Li,

Ji‐Yu Tao

et al.

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

Published: April 10, 2025

This study describes an efficacious and generally applicable synthetic strategy for the incorporation of biologically physiologically prominent difluoromethyl entity into synthetically crucial hydrazone scaffolds with bench-stable easily accessible difluoromethyltriphenylphosphonium bromide. The broad substrate scope, excellent functional group compatibility, feasibility step atom economical one-pot manipulation, environmentally benign mild reaction conditions rendered this methodology efficient tool preparation pharmaceutically fluorine-containing imino compounds.

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
Photocatalytic synthesis of polyfluoroalkylated dihydropyrazoles and tetrahydropyridazines DOI

Ling-Li Liu,

Chengli Xiang,

Changduo Pan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(77), P. 10764 - 10767

Published: Jan. 1, 2024

A photocatalytic trifluoromethylation/cyclization reaction of

Language: Английский

Citations

3
Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(18), P. 5143 - 5160

Published: Jan. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Language: Английский

Citations

2
Accessing Structurally Diverse Aryl Difluoromethyl Ethers with Bromo(difluoro)acetic Acid DOI
Sandeep Kumawat, Kishore Natte

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

Published: Jan. 1, 2024

We report a new streamlined approach for the difluoromethylation of ubiquitous phenols using inexpensive bromo(difluoro)acetic acid, yielding wide array structurally diverse OCF

Language: Английский

Citations

2
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

Citations

0