Catalytic reduction of trifluoromethylated alkyl bromides and synthesis of alkylated heterocycles under visible light irradiation: synergetic action of a halogen bond and Ni catalysis DOI

Gai-Rong Wang,

Peng Guo, Guoliang Pu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4722 - 4729

Published: Jan. 1, 2024

The concurrent reduction of α-trifluoromethyl alkyl bromides and the cross-coupling THF with heterocycles in one pot have been realized through synergetic action a halogen bond Ni catalysis.

Language: Английский

Photoredox-Neutral Ni-Catalyzed Decarboxylative Fluoroalkylation via Radical Sorting Cross-Coupling DOI
Yaxing Wu, Xiuling Wang, Zhiyuan Bao

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 8140 - 8149

Published: May 1, 2025

Language: Английский

Citations

0
Visible Light Mediated Palladium-Catalyzed Hydrodebromination of Aliphatic α-Bromotrifluoromethyl Compounds DOI
Jian Zhen Ou,

Pei-Zhen Qu,

Liang Zhao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(4), P. 1334 - 1334

Published: Jan. 1, 2025

Language: Английский

Citations

0
Synthesis of Chiral 3-Piperidin-2-ones and 3-Piperidines via Ni-Catalyzed Reductive Coupling DOI
Zhaoqing Wang, Z. Y. Zhang, Rui Liu

et al.

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

Published: May 13, 2025

Herein, an approach to a wide range of chiral 3-substituted δ-lactams from reductive coupling Csp2-hybridized organohalides and 3-chloro-δ-lactams was described, the products are versatile precursors for accessing enantioenriched piperidines. The utility reaction highlighted by economic synthesis Preclamol Niraparib. Notably, modified Bilm ligands were found be key factor reactivity enantioselectivity.

Language: Английский

Citations

0
Visible Light Catalyzed Reductive Cross‐Coupling of α‐CF3‐alkyl Bromide and Alkynyl Bromide† DOI

Yiqiang Tian,

Yi Li, Chun Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(20), P. 2479 - 2484

Published: June 21, 2024

Comprehensive Summary Traditional reduction coupling reactions of two bromides typically rely on transition metal catalysis. Here, we introduce the development a visible‐light catalytic direct reaction between α ‐CF 3 ‐alkyl and alkynyl to access valuable organic frameworks. Our research confirms excellent compatibility this with various functional groups, which could be used modify substrate biologically active molecular fragments. Mechanistic investigations, including control experiments, fluorescence quenching studies, light‐switching have provided insights into mechanism. This study paves way for application catalysis in diverse synthetic transformations, offering sustainable efficient approach synthesis.

Language: Английский

Citations

3
Nickel-Catalyzed Hydrotrifluoroalkylation of Alkynes to Construct Allylic Trifluoromethyl Terminal Alkenes DOI
Ting Zhang,

Ya-Wen Zuo,

Ruo‐Xing Jin

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3578 - 3584

Published: May 9, 2023

Herein, we describe a nickel-catalyzed hydrotrifluoroalkylation of terminal alkyne for the synthesis manifold allylic trifluoromethyl alkene. The combination nitrogen and phosphine ligands, especially electron-rich ones, plays an indispensable role in course reaction, promoting reactivity to remarkable level, demonstrating high efficiency, broad substrate scope, favorable functional group compatibility. strategy provides facile method diversified CF3-containing drugs bioactive molecules.

Language: Английский

Citations

7
Nickel-Catalyzed Reductive Decarboxylative/Deaminative Glycosylation of Activated Aliphatic Acids and Primary Amines DOI
Xu‐Ge Liu, Qian Yang,

Deng-Yin Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 5022 - 5026

Published: July 3, 2023

This study describes the nickel-catalyzed reductive decarboxylative/deaminative glycosylation of activated aliphatic acids/amines. Various alkyl C-glycosides were efficiently constructed under simple and mild reaction conditions. The reactions high-yielding exhibited a broad substrate scope, thereby enabling transformation some structurally complex natural products late-stage modifications drugs.

Language: Английский

Citations

7
Advances in Direct Fluoroalkylation of Organic Substrates with Partially Fluorinated Alkyl Motivs DOI
Sebastián Barata‐Vallejo, Sergio M. Bonesi, Al Postigo

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(21), P. 15879 - 15907

Published: Oct. 11, 2024

Partially fluorinated alkyl groups other than methyl are increasingly playing crucial roles in the development of drugs with diverse biological activities, thus creating an innovative chemical space within organofluorine chemistry. For studies structure–activity relationships, late-stage modification such or substituents into substrates that bear activity is essential. This perspective will study catalytic protocols for direct introduction partially monofluoroalkylated (−CHFR, –CH2CH2F), difluoroalkylated (−CF2Me, –CH2CF2H), trifluoroalkylated (−CHR(CF3), –CH2CF3, –CH2CH2CF3, –CH(Me)CF3, –C(Me)2CF3), and pentafluoropropylated (−CH2C2F5) onto (hetero)aromatic compounds, double bonds, isonitriles, halides, N, O, S atoms.

Language: Английский

Citations

2
Redox-neutral decarboxylative coupling of fluoroalkyl carboxylic acids via a dual metal photoelectrocatalysis DOI Creative Commons
Yaxing Wu, Xiuling Wang, Zhenyu Wang

et al.

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

Published: Jan. 1, 2024

Given the importance and beneficial characteristics of aliphatic CF

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
Synthesis of chiral allylic phosphonates via asymmetric reductive cross-coupling of α-bromophosphonates and vinyl bromides DOI

Hepan Wang,

Xinxuan Li, Tao Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(9), P. 2621 - 2625

Published: Aug. 16, 2023

Language: Английский

Citations

6