Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine DOI

Yupian Deng,

Yuhao Qian,

Jia‐Qi Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

A base-controlled synthesis of N -β-CF 3 -substituted 2 H -benzo[ d ]imidazole-2-thiones and 2-fluoro-4 -benzo[4,5]imidazo[2,1- b ][1,3]thiazines via hydroamination or defluorinative cyclizations α-CF -styrenes with 2-mercaptobenzimidazole was developed.

Language: Английский

Water-Controlled Geminal Hydroxyphosphinoylation and Diphosphinoylation of Enaminones with H-Phosphine Oxides DOI

Qiang Huang,

Xin Jin, Huabin Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

A water-controlled geminal phosphinoylation of enaminones with H-phosphine oxides has been established through AlCl3-mediated C-N bond cleavage in this work, which provides a novel strategy for accessing various hydroxy and diphosphinoyl products 3a 4a high yields. The transformation features excellent functional group tolerance, operational simplicity, atom economy, is amenable complex molecule skeletons. Preliminary mechanism studies suggest the conversion from to involve elimination hydroxyl group, water temperature plays critical role influencing reaction pathway product selectivity. This research significant value functionalization enaminones.

Language: Английский

Citations

0
Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes DOI

Pai Zheng,

Yupian Deng,

Jingjing He

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(3)

Published: Jan. 8, 2024

Abstract An efficient and practical method for the synthesis of (β‐trifluoromethyl‐β‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation α‐(trifluoromethyl)styrenes with pyridine‐2(1 H )‐thione was reported. The reaction proceeded smoothly regioselectively in an anti‐Markovnikov manner assistance DBU afforded a variety trifluoromethyl‐containing moderate to good yields.

Language: Английский

Citations

3
Two-step synthesis of vicinal trifluoromethyl primary amines from α-(trifluoromethyl)styrenes and phthalimide DOI

Ying Liu,

Jia‐Qi Huang,

Zhudi Sun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4641 - 4646

Published: Jan. 1, 2024

A novel two-step synthesis of β-trifluoromethyl primary amines from readily available α-(trifluoromethyl)styrenes and phthalimide is developed. The first step involves a hydroamination between (PhthNH) with the assistance base. Next, hydrazinolysis resulting

Language: Английский

Citations

2
Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF3 tertiary alcohols DOI

Min-Ming Lu,

Ning Deng, Shiyu Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(15), P. 8694 - 8700

Published: Jan. 1, 2024

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes under an air atmosphere was developed to construct densely functionalized α-CF 3 tertiary alcohols.

Language: Английский

Citations

1
Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes DOI
Jun Pan, Yuting Feng, Leiyang Lv

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 22, 2024

Abstract A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides HOO t Bu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, β ‐peroxy‐phosphine were selectively obtained catalytic amount base, while addition acid led to exclusive formation ‐keto‐phosphine control experiments showed that could also act HAT‐catalyst induce O−O bond cleavage peroxides acidic

Language: Английский

Citations

1
Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P DOI Creative Commons
Yifan Liu,

Ronghai Cui,

Jialing Kang

et al.

Zeitschrift für Kristallographie - New Crystal Structures, Journal Year: 2024, Volume and Issue: 239(4), P. 731 - 733

Published: May 31, 2024

Abstract C 21 H 18 BrO 3 P, monoclinic, P 2 1 / c (no. 14), a = 20.2890(9) Å, b 5.9736(2) 16.1577(8) β 105.371(2)°, V 1888.24(14) Å , Z 4, R gt ( F ) 0.1359, w ref 0.1414, T 298.00 K.

Language: Английский

Citations

0
Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine DOI

Yupian Deng,

Yuhao Qian,

Jia‐Qi Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

A base-controlled synthesis of N -β-CF 3 -substituted 2 H -benzo[ d ]imidazole-2-thiones and 2-fluoro-4 -benzo[4,5]imidazo[2,1- b ][1,3]thiazines via hydroamination or defluorinative cyclizations α-CF -styrenes with 2-mercaptobenzimidazole was developed.

Language: Английский

Citations

0