Recent Developments of Stetter Reaction A Brief Review DOI Creative Commons

Jawad K. Shneine,

Shayma Muhsen Ahmad,

Dhea Sh. Zagheer

et al.

Biomedicine and Chemical Sciences, Journal Year: 2022, Volume and Issue: 1(4), P. 234 - 240

Published: Oct. 1, 2022

In this short review definition, mechanism, and recent developments of the Stetter reaction, in period last ten years from 2011 to 2021 are presented. This reaction comprises N-heterocyclic carbene (NHC)-catalyzed umpolung aldehydes followed by their capturing with activated carbon-carbon double bonds (Michael acceptors). work includes also progresses inter-molecular intra-molecular versions enantioselective transformations. Underscoring advances applications synthesis various heterocyclic systems total natural products have been introduced.

Language: Английский

Synthetic Advantages of Defluorinative C−F Bond Functionalization DOI Creative Commons
Leidy V. Hooker, Jeffrey S. Bandar

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Aug. 22, 2023

Abstract Much progress has been made in the development of methods to both create compounds that contain C−F bonds and functionalize bonds. As such, are becoming common versatile synthetic functional handles. This review summarizes advantages defluorinative functionalization reactions for small molecule synthesis. The coverage is organized by type carbon framework fluorine attached mono‐ polyfluorinated motifs. main challenges, opportunities advances discussed each class organofluorine. Most text focuses on case studies illustrate how defluorofunctionalization can improve routes targets or properties enable unique mechanisms reactions. broader goal showcase incorporating exploiting design routes, improvement specific advent new methods.

Language: Английский

Citations

60

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks DOI

Yaopeng Liu,

Qingyu Tian,

Jin Ge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

Citations

12

Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives DOI

Zuguang Yang,

Guangming Wei,

Zhengkai Chen

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(33), P. 4872 - 4890

Published: Jan. 1, 2023

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized discussed. The cascade annulation reactions synthons with suitable coupling partners have emerged as a powerful promising tool for construction variety trifluoromethyl-substituted heterocycles. Compared other building blocks, TFAICs derivatives notable merits easy availability handling, relative stability safety, high reactivity.

Language: Английский

Citations

23

Difluoromethylation of heterocyclesviaa radical process DOI
Linlin Shi,

Dongdong An,

Guang‐Jian Mei

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(15), P. 4192 - 4208

Published: Jan. 1, 2022

In this review, we summarize the state-of-the-art advances in difluoromethylation of heterocycles via a radical process over past few years (2018 to early 2022).

Language: Английский

Citations

24

Recent advances in C–F bond activation of trifluoromethylated carbonyl compounds and derivatives DOI

Xuanming Gong,

Qin Zhou, Guobing Yan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(27), P. 5365 - 5376

Published: Jan. 1, 2022

The selective functionalization of inert C–F bonds in trifluoromethylated carbonyl compounds has been summarized and the reaction mechanisms are also discussed.

Language: Английский

Citations

23

BF3-Promoted Ring Expansion of Iminylphosphiranes and Acylphosphiranes for Divergent Access to 1,2-Azaphospholidines and 1,2-Dihydrophosphetes DOI
Mingyue Cui, Yang Xu, Rongqiang Tian

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1819 - 1823

Published: Feb. 28, 2024

Ring expansion of strained small rings provides an efficient method for the synthesis various high-value carbocycles and heterocycles. Here we report BF3·Et2O as both activating reagent fluorine source, enabling ring phosphirane P–F bond formation. Treatment 1-iminylphosphirane complexes with resulted in 1,2-azaphospholidines, while reaction 1-acylphosphirane afforded 1,2-dihydrophosphetes. The path was tuned by nucleophilicity N O atoms toward intermediate phosphenium cation.

Language: Английский

Citations

4

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

Synthesis of α-CF3 Amides via Palladium-Catalyzed Carbonylation of 2-Bromo-3,3,3-trifluoropropene DOI Creative Commons

Xiao Rui Wen,

Wen Qing Zhu,

Cai Lin Zhang

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(7), P. 7128 - 7134

Published: Feb. 8, 2023

Amide compounds are important organic compounds, which play an role in biomedical chemistry, materials science, life and other fields. The synthesis of α-CF3 amides, especially containing 3-(trifluoromethyl)-1,3,4,5-tetrahydro-2H-benzo[b][1,4]diazepine-2-one, has long been a challenge due to the tensile properties instability rings. Here, we report example palladium-catalyzed carbonylation CF3-containing olefin form acrylamide. By controlling ligands, can get different amide as products. This method good substrate adaptability functional group tolerance.

Language: Английский

Citations

7

Multi-substituted trifluoromethyl alkene construction via gold-catalyzed fluoroarylation of gem-difluoroallenes DOI Creative Commons
Zhiqiang Li,

Haijun Tang,

Zaixin Wang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(10), P. 3524 - 3529

Published: Jan. 1, 2024

A visible-light-promoted gold-catalyzed fluoroarylation of gem -difluoroallenes is developed. This reaction proceeds in a highly stereo- and regioselective manner enables facile construction tri- tetra-substituted trifluoromethyl alkenes.

Language: Английский

Citations

2

Copper-Catalyzed Synthesis of 4-CF3-1,2,3-Triazoles: An Efficient and Facile Approach via Click Reaction DOI Creative Commons

Tinghong Tang,

Cuiting Chen,

Xin Fu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(6), P. 1191 - 1191

Published: March 7, 2024

Incorporation of a trifluoromethyl group with 1,2,3-triazoles motifs was described. We explored click reaction approach for regioselective synthesis 1-susbstituted-4-trifluoromethyl-1,2,3-triazoles in which 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reacts commercial 2-bromo-3,3,3-trifluoropropene (BTP) to form 3,3,3-trifloropropyne (TFP) situ. Arising from merits associated the availability and stability BTP, high efficiencies CuI/1,10-Phenanthroline (Phen)-catalyzed cycloaddition reactions azides alkynes, this readily performed process takes place target yields, wide azide substrate scope. The potential value protocol demonstrated by its application gram-scale reaction.

Language: Английский

Citations

2