One-Pot Synthesis of Tetrahydro-2H-selenopyran Derivatives from Benzalacetones, Elemental Selenium, and Sodium Borohydride DOI Open Access
Dongdong Chen,

Xufeng Yang

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1641 - 1641

Published: Jan. 1, 2024

摘要 报道了一种以苄叉丙酮、 硒粉和硼氢化钠为原料, 采用一锅法合成一系列四氢-2H-硒吡喃衍生物的新方法.此反 应通过形成 6 个新的化学键很好的构建一系列含硒六元环. 得到了 20 个含有四氢

Lewis Acid Promoted Vicinal Oxytrifluoromethylselenolation of Alkenes DOI
Yang Li,

Shangbiao Zhang,

Yanan Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3210 - 3215

Published: April 28, 2023

Herein, we have developed a metal-free, Lewis acid promoted vicinal oxytrifluoromethylselenolation of alkenes using trifluoromethyl selenoxides as electrophilic trifluoromethylselenolation reagents and alcohols nucleophiles. With less steric good nucleophilic solvents (such ethanol methol), Tf2O-catalyzed could be realized, while stoichiometric Tf2O was required to promote full transformation with isopropanol tert-butanol). The reaction featured substrate scope, functional group compatibility, diastereoselectivity. This method further applied oxytrifluoromethylselenolation, aminotrifluoromethylselenolation nucleophiles under modified conditions. A mechanism involving seleniranium ion proposed based on the preliminary results.

Language: Английский

Citations

14
Visible-Light Photocatalytic Synthesis of Difluoromethylated Selenides from Selenosulfonates through a Radical Process DOI
Yi Fang, Chunyi Liu, Jie Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12658 - 12667

Published: Aug. 18, 2023

A photocatalytic synthesis of difluoromethylated selenides from selenosulfonates is described here. Bench-stable difluoromethyl phosphonium salt [Ph3PCF2H]Br reacts smoothly with to give a series functionalized in moderate good yields via radical process. This protocol free stoichiometric base and reductant, has tolerance functional groups, successful late-stage modification bioactive molecules, which provides facile access molecules pharmaceutical relevance.

Language: Английский

Citations

9
Photoinduced Copper-Promoted Decarboxylative Trifluoromethylselenolation of Aromatic Carboxylic Acids with [Me4N][SeCF3] DOI
Lei Liu, Yu‐Cheng Gu, Cheng‐Pan Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 9372 - 9380

Published: June 21, 2023

Visible-light-induced decarboxylative trifluoromethylselenolation of (hetero)aromatic carboxylic acids with [Me4N][SeCF3], oxidant, and catalysts afforded a variety (hetero)aryl trifluoromethyl selenoethers in good yields. The reaction might involve radical process, which generated radicals from the stable via oxidative decarboxylation NFSI as [di-tBu-Mes-Acr-Ph][BF4] photocatalyst, 1,1'-biphenyl cocatalyst. Both had decisive influence on reaction. was further promoted by copper salts probably Cu-mediated cross-coupling sensitive SeCF3 species situ formed radicals. Advantages method include visible light irradiation, mild conditions at ambient temperature, functional group tolerance, no pre-functionalization/activation starting acids, applicability to drug molecules. This protocol is promising synthetically useful, overcame limitations known methods represented first acids.

Language: Английский

Citations

8
Tf2O‐Catalyzed Tandem Cyclization/Trifluoromethylselenolation of Alkynes for Synthesis of CF3Se‐Containing Heterocycles DOI

Shangbiao Zhang,

Yan Gao, Rui Xiao

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(41)

Published: May 8, 2023

Herein, the tandem synthesis of various CF3 Se-containing heterocyclic compounds has been developed, using Tf2 O as catalyst and trifluoromethyl selenoxides electrophilic trifluoromethylselenolation reagents. This process is characterized by its mild conditions, ease operation, good functional group compatibility. A variety alkynes could be transferred into indoles, benzofurans, benzothiophenes, isoquinolines chromenes in yields. key step involving formation Se species was proposed.

Language: Английский

Citations

7
Direct Trifluoromethylselenolation and Fluoroalkylselenolation of C−H Bonds: Recent Advances in Reagents Development and Reactions DOI
Yan Gao, Rui Xiao,

Shangbiao Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(38)

Published: Aug. 3, 2023

Abstract Due to their high lipophilicity and strong electron‐withdrawing property, more attention has been paid introducing trifluoromethylseleno fluoroalkylseleno moieties into organic molecules. In this short review, we categorize the synthesis of compounds that combine selenium fluorinated two main types: trifluoromethylselenolation (CF 3 Se) fluoroalkylselenolation (R f Se, except CF Se). This review aims provide a summary recent advances in direct C−H from reagents application. Based on method how R Se group was introduced, content is divided three parts: transition‐metal‐free reactions, transition‐metal‐mediated/catalyzed reactions photo‐catalyzed reactions. The general substrate scope, mechanism limitations would also be discussed so hope will serve as an inspiration for further research appealing field.

Language: Английский

Citations

7
Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes DOI
Yan Gao, M. Xiao,

Bingbing Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4905 - 4911

Published: Jan. 1, 2023

Herein, we have reported a metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes to construct α-trifluoromethylselenolated ketones and trifluoromethylselenolated alkynes.

Language: Английский

Citations

5
Photocatalytic Perfluoroalkylation of Disulfides and Diselenides. Syntheses of Perfluoroalkyl Thio- and Seleno-ethers DOI
Romina S. Conde,

Loydel Torres Barroso,

Sheila G. Pérez Edighill

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10867 - 10877

Published: July 22, 2024

The synthesis of alkyl(aryl)-fluoroalkyl sulfanyl [R(Ar)-S-R

Language: Английский

Citations

1
Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization DOI Open Access
Jia Wang, Jiaqi Niu,

Mingjiang Geng

et al.

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

Published: Oct. 15, 2024

Abstract An expedient strategy for the construction of trifluoromethylselenolated spiro[5.5]trienones/spiro[4.5]trienones through a cascade electrophilic trifluoromethylselenolation cyclization and dearomatization has been developed. This sequential process was induced by N ‐trifluoromethylselenophthalimide (Phth‐SeCF 3 ), which an efficient reagent. approach feature mild conditions, broad substrate scope, high functional group tolerance.

Language: Английский

Citations

0
Modular trifluoromethylselenolation and fluoroalkylselenolation via Ag(I)-mediated selenium nitrogen exchange reaction of benzothiaselenazole-1-oxides DOI Creative Commons

Xinyue Lin,

Chensi Li,

Zeqin Zhuang

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 1, 2024

Language: Английский

Citations

0
One-Pot Synthesis of Tetrahydro-2H-selenopyran Derivatives from Benzalacetones, Elemental Selenium, and Sodium Borohydride DOI Open Access
Dongdong Chen,

Xufeng Yang

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1641 - 1641

Published: Jan. 1, 2024

摘要 报道了一种以苄叉丙酮、 硒粉和硼氢化钠为原料, 采用一锅法合成一系列四氢-2H-硒吡喃衍生物的新方法.此反 应通过形成 6 个新的化学键很好的构建一系列含硒六元环. 得到了 20 个含有四氢

Citations

0