Six-membered ring systems: With O and/or S atoms DOI
Clementina M.M. Santos, Artur M. S. Silva

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 493 - 568

Published: Jan. 1, 2023

Language: Английский

Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones DOI

Longhui Wu,

Xia Liu,

Zhao-Wen Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9236 - 9241

Published: Jan. 1, 2023

A convenient and efficient method for the synthesis of difluoro/trifluoromethyl carbinol-containing chromone derivatives has been developed.

Language: Английский

Citations

13
Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation DOI
Prasanta Ray Bagdi, Karuna Mahato,

Divya Shrestha

et al.

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

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

Citations

5
Research Progress on Direct Trifluoromethylselenylation DOI Open Access

Zhaoming Hu,

Jihong Wu,

Jingjing Wu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(1), P. 36 - 36

Published: Jan. 1, 2023

The trifluoromethylselenylation reaction is another important research topic after trifluoromethylsulfanylation in recent years.Because the trifluoromethylselenyl group contains two chemical elements, fluorine and selenium, compounds containing trifluoromethyl selenide have potential biological activities, more researchers begin to turn their attention this new years.In paper, according three types of nucleophilic reaction, electrophilic radical results domestic foreign scholars on direct 6 years are comprehensively summarized, some mechanisms discussed detail.Finally, summarized prospected.

Language: Английский

Citations

10
An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones DOI
Liu‐Liang Mao, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110784 - 110784

Published: Dec. 1, 2024

Language: Английский

Citations

4
Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones DOI
Jinwei Yuan, Qiang Liu,

X. H. Liu

et al.

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

Published: April 22, 2025

A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported N-trifluoroethylaminopyridinium salt was achieved in the absence transition metal catalysts or bases. Notable features this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that reaction proceeds via radical pathway, involving an situ generated N-trifluoroethyl radical, followed by 1,2-H shift.

Language: Английский

Citations

0
Visible-Light-Promoted Trifluoromethylthiolation and Trifluoromethylselenolation of 1,4-Dihydropyridines DOI

Xiwen Shan,

Xiaoxing Wang,

Enxue Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 319 - 328

Published: Dec. 27, 2022

We report a metal-free trifluoromethylthiolation and trifluoromethylselenolation of 1,4-dihydropyridines with S-(trifluoromethyl) 4-methylbenzenesulfonothioate Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate under visible light irradiation. This transformation was tolerated wide range functional groups provided an alternative green strategy for the synthesis trifluoromethylthioesters trifluoromethylselenoesters.

Language: Английский

Citations

13
Visible-light-enabled cascade cross-dehydrogenative-coupling/cyclization to construct α-chromone substituted α-amino acid derivatives DOI
Zhi‐Qiang Zhu, Jiayu Hu, Zongbo Xie

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 60(1), P. 106 - 109

Published: Nov. 24, 2023

Organophotocatalytic cascade cross-dehydrogenative-coupling/cyclization reaction of o-hydroxyarylenaminones with α-amino acid derivatives for the construction α-chromone substituted was developed. Various N-arylglycine esters, amides and dipeptides underwent cyclization well to afford corresponding 3-aminoalkyl chromones in good excellent yields. This approach consists visible-light-promoted oxidation derivatives, Mannich reaction, intramolecular nucleophilic under acidic conditions, features a wide scope, simple operation mild which may have potential be used synthesis bioactive molecules.

Language: Английский

Citations

6
Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions DOI
Fei Li,

Jiawei Song,

Cheng‐Pan Zhang

et al.

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

Published: May 29, 2024

Abstract The trifluoromethylthio (SCF3) and trifluoromethylselanyl (SeCF3) groups possess high electron-withdrawing ability, excellent lipophilicity, good stability, bioavailability, they are promising structural motifs in drug design development. Photoredox catalysis has clear benefits; it is a mild sustainable methodology for the modification of chemical structures that enables variety reactions unattainable using classical ionic chemistry. This review focuses on light-initiated trifluoromethylthiolation trifluoromethylselenolation with diverse SCF3 SeCF3 reagents. Representative transformations either photocatalysts or through EDA complexes, as well possible reaction mechanisms, all discussed this article. 1 Introduction 2 Photocatalyzed Trifluoromethylthiolation 2.1 MSCF3 (M = H, [Me4N], Ag) 2.2 XSCF3 (X Cl, CF3S) 2.3 ArSO2SCF3 2.4 N–SCF3 Reagents 2.5 Other 3 Trifluoromethylselenolation 3.1 [Me4N][SeCF3] 3.2 ArSO2SeCF3 4 Summary

Language: Английский

Citations

2
Copper-catalyzed ring-opening trifluoromethylthiolation/trifluoromethylselenolation of cyclopropanols with TsSCF3orSe-(trifluoromethyl) 4-methoxybenzenesulfonoselenoate DOI

Ankun Li,

Xiaoxing Wang, Yuqing Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(17), P. 3675 - 3683

Published: Jan. 1, 2023

We report a ring-opening trifluoromethylthiolation of cyclopropanols with TsSCF3 by using Cu(OAc)2 as the catalyst. Moreover, this strategy, trifluoromethylselenolation Se-(trifluoromethyl) 4-methoxybenzenesulfonoselenoate to access β-SeCF3-substituted carbonyl compounds is achieved for first time. The broad substrate scope, readily accessible reagents and cheap catalyst make protocol an alternative efficient method synthesis β-SCF3-substituted or compounds.

Language: Английский

Citations

2
Nickel‐Catalyzed Electrochemical Synthesis of (Hetero)Aryl Trifluoromethyl Selenides DOI Creative Commons
Serhii Krykun, Muriel Durandetti

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 26(4)

Published: Dec. 13, 2022

Abstract A convenient and efficient approach for the construction of aryl trifluoromethyl selenoethers from iodides under mild conditions is reported. Electrochemical activation stable inexpensive NiBr 2 bipy (bipy – bipyridine) complex instead labile Ni(COD) (COD cyclooctadiene) catalyst. [NMe 4 ][SeCF 3 ] employed as shelf‐stable source SeCF fragment. The reaction tolerates a wide range substrates, including modification drug‐like molecules. Cyclic voltammetry studies allow insight into mechanism.

Language: Английский

Citations

3