Cited by Hydroazidation of trifluoromethyl alkenes with trimethylsilyl azide enabled by organic photoredox catalysis

Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF₃SO₂Na: facile access to α,β-bistrifluoromethyl tertiary alcohols DOI

Pai Zheng,

Chuan Liu,

Qianding Zeng

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(47), P. 9302 - 9306

Published: Jan. 1, 2022

A mild and practical Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF3SO2Na in the presence K2S2O8 air was developed. The reaction proceeded efficiently at room temperature without β-fluoride elimination afforded corresponding α,β-bistrifluoromethyl tertiary alcohols good to excellent yields.

Language: Английский

Citations

Controllable Synthesis of Trifluoromethyl- or gem-Difluorovinyl-containing Analogues of Neonicotinoids by the Reaction of α-(Trifluoromethyl)styrenes with 2-Nitroimino-imidazolidine DOI

Jingjing He,

Zhudi Sun,

Yupian Deng

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(8), P. 3530 - 3530

Published: April 17, 2023

A simple and straightforward addition or defluorination of α-(trifluoromethyl)styrenes with 2-nitroimino-imidazolidine (2a), 2-(nitromethylene)imidazolidine (2b), 2-cyanoimino-thiazolidine (2c), (E)-1-methyl-2-nitroguanidine (2d), in a controlled manner, was developed. The hydroamination 2a, 2b, 2c, 2d completed the presence DBN at room temperature within 0.5–6 h, affording structurally diverse β-trifluoromethyl-β-arylethyl analogues neonicotinoids moderate to good yields. γ,γ-difluoro-β-arylallyl were also successfully synthesized via α-(trifluoromethyl)styrenes, 2a 2c using NaH as base an elevated together prolonged reaction time 12 h. method features setup, mild conditions, broad substrate scope, high functional group compatibility, easy scalability.

Language: Английский

Citations

Solvent-Dependent Rhodium-Catalyzed Divergent Hydrofunctionalization of Trifluoromethylalkenes DOI

Junhan Ma,

Philippe Jubault, Samuel Couve‐Bonnaire

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(26), P. 4928 - 4933

Published: June 23, 2023

We report a rhodium-catalyzed anti-Markovnikov regioselective hydrosilylation of trifluoromethylalkenes with substituted silanes giving various α-trifluoromethyl-β-silanes in good to excellent yields. The hydrogenation products were obtained via the same key intermediate treated methanol as protic solvent. Both transformations had broad functional tolerance and expected facilitate construction complex α-trifluoromethyl compounds.

Language: Английский

Citations

Synthesis of α-(Trifluoromethyl)styrenes and 1,3-Di(trifluoromethyl)indanes via Electrophilic Activation of TMS Ethers of (Trifluoromethyl)benzyl Alcohols in Brønsted Acids DOI

Olesya V. Khoroshilova, Irina А. Boyarskaya, Aleksander V. Vasilyev

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(23), P. 15845 - 15862

Published: Nov. 17, 2022

TMS ethers of CF3-benzyl alcohols (and their heterocyclic analogues) undergo elimination TMSOH molecule with the formation α-(trifluoromethyl)styrenes in yields up to 90% under action strong Brønsted acids TfOH or H2SO4. Under acidic conditions upon prolongation reaction, are further dimerized into cis-/trans-1,3-di(trifluoromethyl)indanes 100%. Plausible reaction mechanisms these electrophilic transformations including intermediate carbocations discussed.

Language: Английский

Citations

Hydroazidation of trifluoromethyl alkenes with trimethylsilyl azide enabled by organic photoredox catalysis DOI

Yutao Shi,

Yuliang Zhang, Xiaochen Ji

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(60), P. 7741 - 7744

Published: Jan. 1, 2024

A mild hydroazidation of trifluoromethyl alkenes with trimethylsilyl azide through organic photoredox catalysis was developed, delivering a series valuable β-CF 3 -azides exclusive selectivity.

Language: Английский

Citations