Condition‐Controlled Selective Synthesis of CF3‐Chromene and CF3‐Benzofuran from N‐Phenoxyacetamide and CF3‐Ynone DOI Open Access

Huihang Hou,

Shengnan Yan,

Yuanshuang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

Photoinduced C–H heteroarylation of enamines via quadruple cleavage of CF2Br2 DOI

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6112 - 6116

Published: Jan. 1, 2023

The C–H functionalization of enamines has attracted much attention over the past few years; however, heteroarylation still remains rare.

Language: Английский

Citations

70

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

Citations

66

Radical relay cyclization/C–C bond formation of allyloxy-tethered aryl iodides with quinoxalin-2(1H)-ones via polysulfide anion photocatalysis DOI
Zhongyi Zhang, Yaqin Zhou, Jiehui Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(8), P. 1708 - 1713

Published: Jan. 1, 2024

A visible-light-induced radical relay cyclization/C-C bond formation of quinoxalin-2(1

Language: Английский

Citations

26

Regioselective C3Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles DOI
Ruiqin Zhang,

Renchao Ma,

Rener Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1846 - 1857

Published: Jan. 12, 2024

Herein, we describe an efficient transition-metal-free regioselective C3alkylation of indoles for the synthesis bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as oxidant to oxidize alcohols in presence a strong base reaction avoids use transition metals such Ru Mn. The protocol provides favorable route access biologically active compounds arundine, vibrindole A, turbomycin B.

Language: Английский

Citations

19

Divergent Synthesis of Four Types of Fused N‐Containing Heterocycles via Oxidative Multi‐Component Cyclization Reaction DOI Open Access

Xiaoshuang Guo,

Maozhong Miao, Peng Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Comprehensive Summary An atmospheric‐oxygen‐mediated four‐component reaction was developed for the divergent synthesis of pyrazolo[1,5‐ a ]pyrimidine and pyrazolo[3,4‐ b ]pyridine derivatives from readily available alcohols 3‐aminopyrazoles. In this transformation, atmospheric oxygen serves as green oxidant, promoting equivalent aldehydes four types N ‐containing heterocycles (> 40 examples). Remarkably, transformation features metal‐free molecular diversity.

Language: Английский

Citations

4

Chloride‐Promoted Photoelectrochemical C—H Silylation of Heteroarenes DOI

Xin‐Ru Zhao,

Yu‐Chen Zhang,

Zhong‐Wei Hou

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(22), P. 2963 - 2968

Published: June 24, 2023

Comprehensive Summary A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H 2 evolution has been developed. The depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated light‐induced homolytic cleavage Cl , in which was produced by electrochemical oxidation chloride. large number silylated heterocyclic molecules are rapidly constructed satisfactory yields without relying oxidants and metal reagents.

Language: Английский

Citations

40

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds DOI
Peng Zhao, Yanbo Liu, Yuting Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2511 - 2516

Published: March 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Language: Английский

Citations

18

Copper-catalyzed divergent construction of naphthofurans and benzochromanes from 2-naphthols, 4-methylene-quinazolin(thi)ones, and N,N-dimethylethanolamine DOI

Meiqi Geng,

Jinqiang Kuang, Weiwei Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(4), P. 1198 - 1204

Published: Jan. 1, 2024

Cu( ii )-catalyzed divergent synthesis of naphthofurans and benzochromanes through [3 + 2 1] 1 annulations is established.

Language: Английский

Citations

15

Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage DOI
Peng Zhao, You Zhou, Can Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2505 - 2515

Published: Feb. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Language: Английский

Citations

15

Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF3-ynones via C–H/N–H/C–N/C–C bond cleavage DOI
Hao Li,

Shengnan Yan,

Yuanshuang Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Language: Английский

Citations

14