Synthesis of Axially Chiral Monofluoroalkenes via Nickel-Catalyzed Reductive Cross-Coupling of gem-Difluoroalkenes DOI
Tiantian Yin, Ming Yu Jin, Tiantian Zhao

et al.

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

Published: Sept. 13, 2024

Enantioenriched monofluoroalkenes are important structural motifs in life science and functional materials. To date, only limited strategies were reported for the synthesis of with stereogenic carbon centers; axially chiral counterpart is still highly desirable. Herein, we report Ni-catalyzed defluorinative cross-electrophile coupling

Language: Английский

Synthesis of Sterically Hindered Dialkyl Ethers via Palladium-Catalyzed Fluoro-alkoxylation of gem-Difluoroalkenes DOI
Fen Wu, Junbiao Chang, Dachang Bai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4953 - 4957

Published: May 30, 2024

Organofluorine compounds are of high value in medicinal and agricultural chemistry. Herein, we report a palladium-catalyzed fluoro-alkoxylation gem-difluoroalkenes for the synthesis much more challenging sterically hindered ethers. This reaction represents direct method α-trifluoromethyl ethers with broad functional group tolerance excellent regioselectivity. system employs N-fluorobenzenesulfonimide (NFSI) as an electrophilic fluorine source alcohols nucleophilic donors, including but not limited to tert-substituted alcohols.

Language: Английский

Citations

5
Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis DOI

Ya-Fei Hu,

Wei Han,

Ye-Kun Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5144 - 5150

Published: Jan. 1, 2024

A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.

Language: Английский

Citations

4
Transition‐Metal‐Free Carbonyl Reduction and Hydrodefluorination of β‐Trifluoromethyl Enones with Hydrosilanes: Synthesis of gem‐Difluorovinyl Alcohols DOI

Peng‐Yuan Zhang,

Ya‐Fei Hu,

Jia‐Hao Chu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: April 20, 2024

Abstract A tandem carbonyl reduction and hydrodefluorination of β‐trifluoromethyl enones with hydrosilanes under transition‐metal‐free conditions was developed for the synthesis a variety valuable gem ‐difluorovinyl alcohols. The hydrosilane could act as both reductive agent C(sp 3 )‐F bond‐breaking promoter mild reaction conditions. Synthetically useful organofluorides, such ‐fluorophosphine alkene, ketone, fluorinated dihydrofuran derivatives be readily constructed by further transformations obtained Moreover, method features conditions, operational simplicity, excellent functional group tolerance, scalability.

Language: Английский

Citations

2
Facile synthesis of β‐trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation of a‐trifluoromethyl styrenes with thiols DOI

Yupian Deng,

Jia‐Qi Huang,

Yuhao Qian

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(20)

Published: July 23, 2024

Abstract A very simple and atom‐economical method for the synthesis of vicinal trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation α‐(trifluoromethyl)styrenes with thiols was reported. The reaction proceeded smoothly under mild conditions provided β‐CF 3 ‐thioethers in moderate to good yields an anti‐Markovnikov manner. Furthermore, this features several remarkable advantages, such as use a catalytic amount DBN, broad substrate scope, excellent functional group compatibility, easy scalability.

Language: Английский

Citations

1
Transition-Metal-Free Hydrodefluoroamination of Trifluoromethyl Enones for the Synthesis of α-Fluoroenamides DOI

Ya‐Fei Hu,

M Kellis,

Ming-Yao Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10299 - 10310

Published: July 2, 2024

A three-component strategy was developed to enable hydrodefluoroamination of β-trifluoromethyl enones by selectively activating two C(sp3)-F bonds in the trifluoromethyl group. The method involved a sequence carbonyl reduction, hydrodefluorination, and defluoroamination under transition-metal-free conditions. Synthetically useful (E)-stereospecific α-fluoroenamides were obtained good yields with diverse functional group tolerance, which could be easily transformed into valuable organofluorides heterocycles. auxiliary exerts both electronic steric impacts on CF3-alkenes, allowing for controllable selective defluorination.

Language: Английский

Citations

0
Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides DOI
Taylor Semeniuk, Ty Dudas,

Esther Okeh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13669 - 13677

Published: Sept. 4, 2024

A photocatalytic process was devised to synthesize monofluoroalkenes via defluorinative functionalization of allylic difluorides.

Language: Английский

Citations

0
Synthesis of Axially Chiral Monofluoroalkenes via Nickel-Catalyzed Reductive Cross-Coupling of gem-Difluoroalkenes DOI
Tiantian Yin, Ming Yu Jin, Tiantian Zhao

et al.

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

Published: Sept. 13, 2024

Enantioenriched monofluoroalkenes are important structural motifs in life science and functional materials. To date, only limited strategies were reported for the synthesis of with stereogenic carbon centers; axially chiral counterpart is still highly desirable. Herein, we report Ni-catalyzed defluorinative cross-electrophile coupling

Language: Английский

Citations

0