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

A quick access to CF3-containing functionalized benzofuranyl, benzothiophene and indolyl heterocycles under catalyst-free conditions DOI

Ayazoddin Aunoddin Kazi,

Nadimpalli Manjuladevi,

Salla Suresh Kumar

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(70), P. 9376 - 9379

Published: Jan. 1, 2024

A catalyst-free one-pot synthetic protocol is presented for the preparation of CF

Language: Английский

Citations

2
Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles DOI

Chenhui You,

Yangjie Huang,

Yi You

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(12), P. 3247 - 3254

Published: Jan. 1, 2022

A copper-mediated three-component reaction for the synthesis of 2-trifluoromethyl benzimidazoles is reported.

Language: Английский

Citations

7
Modular and practical synthesis of gem-difluoroalkenes via consecutive Ni-catalyzed reductive cross-coupling DOI
Jiyang Liu, Xiangzhang Tao,

Zhenlei Zou

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110461 - 110461

Published: Sept. 1, 2024

Language: Английский

Citations

1
Investigation on the inhibition effect and mechanism of hydrogen explosion by 2-bromo-3,3,3-trifluoropropene DOI

Zhangqiang Dong,

Wei Gao, Jiaxing Zhang

et al.

Process Safety and Environmental Protection, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

Language: Английский

Citations

1
Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of Z/E-β-CF3-Enones DOI

Xiao-Ya Yuan,

Zhimin Lü,

Xianqiang Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Condition-controlled switchable and divergent transformations of cost-effective 2-bromo-3,3,3-trifluoropropene (BTP) aldehydes were realized using a decatungstate (TBADT)-photocatalyzed strategy. The hydroacylated products, i.e., β,β-Br,CF

Language: Английский

Citations

1
Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones DOI

Xiao-Ya Yuan,

Jinping Zheng, Xinyu Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

A TBADT-photocatalyzed cascade hydrogen atom transfer procedure was established for the synthesis of α-CF 3 -1,4-diketones from aldehydes and 2-bromo-3,3,3-trifluoro-1-propenes.

Language: Английский

Citations

1
Ru(II)‐Catalyzed Hydroarylation of in situ Generated 3,3,3‐Trifluoro‐1‐propyne by C−H Bond Activation: A Facile and Practical Access to β‐Trifluoromethylstyrenes DOI Creative Commons
Martin Vuagnat, Vincent Tognetti, Philippe Jubault

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(55)

Published: June 23, 2022

In this study, a practical and straightforward synthesis of β-(E)-trifluoromethylstyrenes by ruthenium-catalyzed C-H bond activation was developed. The readily available inexpensive 2-bromo-3,3,3-trifluoropropene (BTP), non-ozone depleting reagent, used as reservoir 3,3,3-trifluoropropyne. With approach, the monofunctionalization panel heteroarenes possible in safe scalable manner (23 examples, up to 87 % yield). Mechanistic investigations density functional theory (DFT) calculations were also conducted get better understanding mechanism transformation. These studies suggested that 1) cyclometallated ruthenium complex enabled transformation, 2) exhibited high efficiency transformation compared commercially [RuCl2 (p-cymene)]2 3) proceeded through bis-cyclometallated intermediate for carboruthenation step.

Language: Английский

Citations

6
Catalytic and Chemodivergent Synthesis of 1-Substituted 9H-Pyrrolo[1,2-a]indoles via Annulation of β-CF3 Enones with 3-Substituted Indoles DOI
Haritha Sindhe,

Nehanaz Saiyed,

Akshay Kamble

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 230 - 244

Published: Dec. 12, 2022

Chemodivergent reactions are more advantageous in organic synthesis that yield diversely functionalized scaffolds from common starting materials. Herein, we report an efficient metal-free chemodivergent protocol for the of 1-substituted 9H-pyrrolo[1,2-a]indole derivatives presence catalytic amounts Lewis acid/Brønsted acid conditions using 3-substituted indoles and β-trifluoromethyl-α,β-unsaturated ketones. Fine-tuning catalyst solvent system reaction deliver trifluoromethyl, trifluoroethylcarboxylate, or carboxylic substituents on C1-position situ. It is postulated LA/BA interaction was found to be crucial C–F activation these transformations.

Language: Английский

Citations

6
Synthesis of Secondary Trifluoromethylated Alkyl Bromides with Further Conversion to Boronic Esters and Alcohols DOI

Weipiao Li,

Ting Mao, Jiajia Yang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(9)

Published: July 31, 2023

Abstract Secondary trifluoromethylated alkyl bromides are versatile building blocks in the synthesis of fluorine‐containing aliphatic compounds. However, current methods preparation limited. In this study, we have developed a general deaminative cross‐coupling Katritzky salts with 2‐bromo‐3,3,3‐trifluoropropene (BTP) as route to α‐trifluoromethylated that is driven by an electron‐donor‐acceptor (EDA) complex. The resultant products can be readily converted α‐trifluoromethyl borates and alcohols, enriching toolbox for synthesizing compounds wide‐ranging applications.

Language: Английский

Citations

2
Synthetic Advantages of Defluorinative C−F Bond Functionalization DOI Creative Commons
Leidy V. Hooker, Jeffrey S. Bandar

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(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

2