Rh(III)-Catalyzed Direct C–H Cyclization of N-Nitrosoanilines with 1,3-Dicarbonyl Compounds: A Route to Tetrahydrocarbazol-4-ones DOI

Liulin Jiao,

Bo Zhang,

Bohong Qu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 10662 - 10669

Published: July 14, 2023

A novel and efficient Rh(III)-catalyzed direct C-H bond tandem annulation of N-nitrosoanilines with 1,3-dicarbonyl compounds through two cleavage was developed. This protocol provides a rapid access to series valuable tetrahydrocarbazol-4-ones the feature readily available starting materials, broad functional group tolerance, in situ generation carbene precursors. Importantly, some reaction products exhibited promising antiproliferative activity cancer cell lines.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

Citations

34
Recent progress in the application of iodonium ylides in organic synthesis DOI
Xia Mi, Chao Pi, Weisheng Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(24), P. 6999 - 7015

Published: Jan. 1, 2022

This review summarizes the recent advances in synthetic application of iodonium ylides covering 2017 to 2022.

Language: Английский

Citations

40
Three-component synthesis ofN-naphthyl pyrazolesviaRh(iii)-catalyzed cascade pyrazole annulation and Satoh–Miura benzannulation DOI

Demao Chen,

Liyun Zhou,

Yunyun Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(27), P. 4036 - 4039

Published: Jan. 1, 2023

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(III) catalysis. synthetic employing simple substrates lead to simultaneous construction dual cyclic moieties, including a pyrazole ring phenyl ring, sequential formation two C-N three C-C bonds.

Language: Английский

Citations

34
Condition-Controlled Selective Synthesis of Pyranone-Tethered Indazoles or Carbazoles through the Cascade Reactions of N-Nitrosoanilines with Iodonium Ylides DOI
Kelin Wang,

Xia Song,

Yongdi Xin

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(24), P. 4422 - 4428

Published: June 8, 2023

Presented herein is a condition-controlled selective synthesis of pyranone-tethered indazoles or carbazole derivatives via the cascade reactions N-nitrosoanilines with iodonium ylides. Mechanistically, formation former involves an unprecedented process including nitroso group-directed C(sp2)–H bond alkylation N-nitrosoaniline ylide followed by intramolecular C-nucleophilic addition to moiety, solvent-assisted cyclohexanedione ring opening, and transesterification/annulation. On contrary, latter initial annulation denitrosation. These developed protocols feature easily controllable selectivity, mild reaction conditions, clean sustainable oxidant (air), valuable products that are structurally diverse. In addition, utility was showcased their facile diverse transformations into synthetically biologically interesting compounds.

Language: Английский

Citations

27
Ru(II)-Catalyzed Decarbonylative Alkylation and Annulations of Benzaldehydes with Iodonium Ylides under Chelation Assistance DOI
Xiang Li, Yang Shen, Guodong Zhang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(29), P. 5281 - 5286

Published: July 18, 2022

A Ru(II)-catalyzed decarbonylative alkylation and annulation of salicylaldehydes 2-aminobenzaldehydes with iodonium ylides has been developed for the synthesis dibenzo[b,d]furans NH-free carbazolones. The reaction proceeds smoothly under mild conditions a low catalyst loading broad substrate compatibility. Notably, hydroxy free amino groups were demonstrated to be effective directing groups, enabling successful aldehyde C–H bond activation subsequent decarbonylation inexpensive Ru(II) catalyst.

Language: Английский

Citations

30
Rhodium(III)‐Catalyzed Divergent C−H Functionalization of N‐Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts DOI
Jie Ren, Yang Liu, Chao Pi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1817 - 1823

Published: Feb. 7, 2023

Abstract We described an Rhodium(III)‐catalyzed divergent C−H bond functionalization of N ‐aryl amidines with iodonium ylides. Carbazolones and zwitterionic salts were diversely constructed through intermolecular annulation intramolecular proton transfer under the different reaction conditions. This protocol is operationally simple tolerates a variety functional groups. The efficient post‐modification pharmaceutical molecules demonstrates its practicability.

Language: Английский

Citations

21
Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization DOI
Xueqing Liu,

Sijia Shi,

Wenqian Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5136 - 5140

Published: June 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Language: Английский

Citations

9
Iodonium ylides: an emerging and alternative carbene precursor for C–H functionalizations DOI
Sanjeev Kumar, Vaishnavi Borkar,

Mohd Mujahid

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(1), P. 24 - 38

Published: Nov. 23, 2022

The metal-catalyzed successive activation and functionalization of arene/heteroarene is one the most fundamental transformations in organic synthesis leads to privileged scaffolds natural products, pharmaceuticals, agrochemicals, fine chemicals. Particularly, transition-metal-catalyzed C-H arenes with carbene precursors via metal migratory insertion has been well studied. As a result, diverse have evaluated, such as diazo compounds, sulfoxonium ylides, triazoles, etc. In addition, there significant developments use iodonium ylides recent years, these reactions proceed high efficiencies selectivities. This review provides comprehensive overview functionalizations, including scope, limitations, their potential synthetic applications.

Language: Английский

Citations

29
Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins DOI
Zi Yang,

Chaoshui Liu,

Jieni Lei

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(97), P. 13483 - 13486

Published: Jan. 1, 2022

A straightforward approach to synthesise isocoumarins via Rh(III)-catalyzed C-H/C-C bond activation/annulation cascade of enaminones and iodonium ylides has been explored. The established protocol is characterized by an exceedingly simple reaction system, high regioselectivity good functional group tolerance. Moreover, this strategy may provide a new route cleavage the C(sp2)-C(O) unstrained ketones.

Language: Английский

Citations

25
The Pyridotriazole Works as a Traceless Directing Group: A C–H Activation/Annulation Cascade Reaction with Iodonium Ylides DOI

Guanghui Lv,

Qingyao Zhang,

Cuimei Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4022 - 4027

Published: May 26, 2023

A novel Rh-catalyzed cascade reaction of pyridotriazoles with iodonium ylides is reported. This one-pot procedure involves a triazole-directed ortho-position C–H carbene insertion, followed by intramolecular denitrogenation annulation. It was noteworthy that this provided straightforward access to 1H-isochromene frameworks excellent yields (up 94% yield).

Language: Английский

Citations

14