2‐Vinylaniline in the synthesis of heterocycles: Recent advances DOI
Fatemeh Doraghi,

Hamed Navid,

Somaye Karimian

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(7), P. 1180 - 1199

Published: May 21, 2024

Abstract 2‐Vinylanilines are readily accessible substrates, which undoubtedly one of the best candidates for construction diversely nitrogen‐containing heterocyclic compounds. Owing to amine and alkenyl groups in their structures, these frameworks offer a facile, direct, selective synthetic method. This review describes various cyclization reactions involving 2‐vinylanilines catalyzed by transition metals, or under metal‐free conditions.

Language: Английский

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications DOI
Mingzhu Lu, Jeffrey Goh, Manikantha Maraswami

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(24), P. 17479 - 17646

Published: Oct. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Language: Английский

Citations

155

The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light DOI Creative Commons
Daniel M. Baier, Carolina Spula,

Stephen Fanenstich

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(20)

Published: Feb. 24, 2023

Photochemical reactors inherently suffer from the low penetration depth of light and therefore rely on high dilutions to enable chemical reactions. Here we present first method UV (ultraviolet) photochemistry in complete absence bulk solvents a ball mill. Triphenylene was synthesized by two routes, Mallory reaction cyclodehydrochlorination (CDHC), resulting yields 81 92 %, respectively. The successfully scaled up gram scale robustness demonstrated for several different substrates. Finally, regioselective assembly nanographenes mechanochemistry larger systems. Thus, mechanochemical approach presented here provides powerful new tool atomically precise construction nanographenes.

Language: Английский

Citations

27

Mechano-photoexcitation for organic synthesis using mechanoluminescent materials as photon sources DOI

Xiaobin Xin,

Jianzhao Geng, Duo Zhang

et al.

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

Published: Nov. 14, 2024

Language: Английский

Citations

6

One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols DOI

Mingshi Pan,

Yixin Tong,

Xiaodong Qiu

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(89), P. 12443 - 12446

Published: Jan. 1, 2022

Herein, a method to access 3-trifluoromethyl-1,4-benzoxazines from CF3-imidoyl sulfoxonium ylides and 2-bromophenols has been demonstrated. This synthetic protocol proceeds via one-pot two-step sequence that includes the lithium-bromide-promoted O-H insertion of annulation, merits broad substrate scope, excellent functional tolerance operational simplicity, which provides an alternative means obtaining CF3-substituted heterocycles.

Language: Английский

Citations

21

Cu-Catalyzed Carbocyclization for General Synthesis of N-Containing Heterocyclics Enabled by BrCF2COOEt as a C1 Source DOI

Xiaofang Song,

Lijing Zhang, Xing‐Guo Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3403 - 3412

Published: Feb. 8, 2024

A practical and efficient copper-catalyzed carbocyclization of 2-functionalized anilines with ethyl bromodifluoroacetate has been developed. Ethyl is employed as the C1 source via quadruple cleavage in this transformation. This reaction can afford a variety N-containing heterocyclics satisfactory yields excellent functional group compatibility.

Language: Английский

Citations

4

[Cp*IrCl2]2-Catalyzed Amidocarbonation of Olefins with Sulfoxonium Ylides toward Functionalized Isoindolin-1-ones DOI
Qi Yang,

Junxue Bai,

Han Yang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7148 - 7153

Published: Sept. 26, 2023

A [Cp*IrCl2]2-catalyzed amidocarbonation of olefins with sulfoxonium ylides has been developed to generate diverse biologically important isoindolin-1-ones in high efficiency under mild reaction conditions. Mechanism studies indicated that this cascade was triggered by amino-iridation the olefin unit iridacycle, followed formal migratory insertion ylides. This newly method features broad substrate scopes and operational simplicity.

Language: Английский

Citations

9

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions DOI Creative Commons
Francesco Mele, Ana Maria Constantin, Andrea Porcheddu

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 458 - 472

Published: March 3, 2025

Photomechanochemistry, i.e., the merger of light energy and mechanical forces, is emerging as a new trend in organic synthesis, enabling unique reactivities fleeting excited states under solvent-minimized conditions. Despite its transformative potential, field faces significant technological challenges that must be addressed to unlock full capabilities. In this Perspective, we analyze selected examples showcase available technologies combine including manual grinding, vortex shaker mixing, rod milling, ball milling. By examining advantages limitations each approach, aim provide an overview current state synthetic photomechanochemistry identify opportunities for future advancements rapidly evolving area research.

Language: Английский

Citations

0

A review on quinolines: New green synthetic methods and bioactive potential DOI Creative Commons
Luana Mota Ferreira, Pilar Garcı́a Garcı́a, Pablo A. García

et al.

European Journal of Pharmaceutical Sciences, Journal Year: 2025, Volume and Issue: unknown, P. 107097 - 107097

Published: April 1, 2025

Quinolines have been an interest of study for a few decades due to the importance this system in natural and pharmaceutical products. Since their discovery nineteenth century, many medicinal properties found quinoline compounds. Firstly, as anti-parasitic agent against malaria then other diseases, such as, parasitic infections, HIV, bacterial infections cancer. Consequently, synthetic methods developed afford ring. In review we look back at traditional forward most recent promising "green" synthesis quinolines. Also, newest advances therapeutic compounds based on skeleton treatment cancer diseases applications derivatives drug delivery systems.

Language: Английский

Citations

0

Recent Advances in the Synthesis of Quinolines: A Focus on Oxidative Annulation Strategies DOI Open Access

Mao-Lin Liao,

Peng-Peng Liu,

Jiacheng Yang

et al.

Catalysts, Journal Year: 2025, Volume and Issue: 15(5), P. 441 - 441

Published: April 30, 2025

Quinoline, a heterocyclic scaffold of paramount importance in medicinal and industrial chemistry, has garnered significant attention due to its versatile application. Traditional synthetic methods, dating back over century, have evolved into innovative strategies leveraging catalytic C–H bond activation, transition-metal-free protocols, photo-induced oxidative cyclization. Recent advancements highlight the synergistic roles catalysts, oxidants, solvents enhancing molecular reactivity reaction efficiency. This review systematically summarizes state-of-the-art annulation techniques for quinoline synthesis, emphasizing mechanistic insights practical applications.

Language: Английский

Citations

0

Unexpected Copper-Catalyzed Cascade Reaction of 1,6-Enynes with Sulfoxonium Ylides DOI
Hong Zhang,

Jieyin He,

Wendi Xu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(39), P. 7095 - 7100

Published: Sept. 26, 2022

An unprecedented copper-catalyzed cascade reaction of 1,6-enynes with sulfoxonium ylides is reported, providing a series structurally intriguing 2,3-disubstituted indolines bearing conjugated dienone functionality at the 3-position in moderate to excellent yields good chemo-, regio-, and diastereoselectivities under mild conditions. Importantly, sulfoxonium-ylide-derived copper-carbene herein exhibits quite different reactivity from that diazo copper-carbene. A rational mechanism, an initial ammonium ylide rather than allene formation, proposed.

Language: Английский

Citations

13