Water-Controlled Geminal Hydroxyphosphinoylation and Diphosphinoylation of Enaminones with H-Phosphine Oxides DOI

Qiang Huang,

Xin Jin, Huabin Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 6, 2025

A water-controlled geminal phosphinoylation of enaminones with H-phosphine oxides has been established through AlCl3-mediated C-N bond cleavage in this work, which provides a novel strategy for accessing various hydroxy and diphosphinoyl products 3a 4a high yields. The transformation features excellent functional group tolerance, operational simplicity, atom economy, is amenable complex molecule skeletons. Preliminary mechanism studies suggest the conversion from to involve elimination hydroxyl group, water temperature plays critical role influencing reaction pathway product selectivity. This research significant value functionalization enaminones.

Язык: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 35(2), С. 108977 - 108977

Опубликована: Авг. 26, 2023

Язык: Английский

Процитировано

63

Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations DOI
Dongsheng Yang, Xiang‐Long Chen, An‐Xin Wu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2665 - 2692

Опубликована: Янв. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Язык: Английский

Процитировано

16

Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization DOI
Haijin Guo, Yunyun Liu, Chengping Wen

и другие.

Green Chemistry, Год журнала: 2022, Номер 24(13), С. 5058 - 5063

Опубликована: Янв. 1, 2022

The electrochemical annulation of enaminones/analogous enamines and thioureas providing 2-aminothiazoles has been realized. Modulating the electrolyte enables diastereoselective synthesis 4,5-dialkoxyl thiazolines by dearomatization.

Язык: Английский

Процитировано

64

Advances in the Transition Metal‐Free C—H Trifluoromethylation DOI

De‐Mao Chen,

Jianwen Jiang, Jie‐Ping Wan

и другие.

Chinese Journal of Chemistry, Год журнала: 2022, Номер 40(21), С. 2582 - 2594

Опубликована: Июль 18, 2022

Comprehensive Summary Trifluoromethyl group is one of the most frequently available and promising functional groups in pharmaceutical, agrochemical as well material molecules. Developing synthetic methods for synthesis trifluoromethyl functionalized compounds by trifluoromethylation reactions occupies significant position modern organic chemistry. On other hand, a typical tool sustainable synthesis, transition metal‐free possesses unique advantages atom economy, easy product purification excellent eco‐tolerance. Consequently, constitute important approaches accessing trifluoromethylated Herein, advances C—H are reviewed first time. According to updated state‐of‐art, both catalytic conventional heating chemistry more photocatalysis included, covering C(sp 3 )–H bond, aromatic 2 bond non‐aromatic different substrates over last five years (2017—2021).

Язык: Английский

Процитировано

41

Cascade in Situ Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones DOI
Yan Lin, Jie‐Ping Wan, Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 4017 - 4023

Опубликована: Март 2, 2023

A facile cascade reaction for the site selective synthesis of 2-cyanochromones is described. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials I2/AlCl3 promoters, products are furnished via tandem chromone ring formation C–H cyanation. The in situ 3-iodochromone a formal 1,2-hydrogen atom transfer (HAT) process account unconventional selectivity. In addition, 2-cyanoquinolin-4-one has been realized by employing corresponding 2-aminophenyl enaminone substrate.

Язык: Английский

Процитировано

23

I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер 36(1), С. 109799 - 109799

Опубликована: Март 20, 2024

Язык: Английский

Процитировано

10

Photocatalytic C–H Thiocyanation of NH2-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones DOI

Junlong Zeng,

Jie‐Ping Wan, Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 13195 - 13203

Опубликована: Сен. 15, 2022

Visible light photocatalytic reactions of NH2-enaminones and ammonium thiocyanate for chemoselective α-C-H thiocyanation have been realized the first time, providing a sustainable route synthesis thiocyanated NH2-enaminones. In addition, enaminone products can be flexibly transformed into 2-aminothiazoles 2-thiazolinones via simple operation.

Язык: Английский

Процитировано

30

Progress in the Study of α-Functionalization of Enaminone DOI Open Access
Ning Liu,

Xiaodan Cuan,

Hui Li

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(2), С. 602 - 602

Опубликована: Янв. 1, 2023

烯胺酮是一类非常重要的有机合成砌块, 具有易获得、储存方便、反应多样性等优点. 更重要的是, 烯胺酮是许 多杂环化合物的重要前体.最近

Язык: Английский

Процитировано

18

Rh-Catalyzed C–H Activation/Annulation of Enaminones and Cyclic 1,3-Dicarbonyl Compounds: An Access to Isocoumarins DOI
Qian Wang, Ying Li,

Jina Sun

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5348 - 5358

Опубликована: Апрель 3, 2023

A facile access to isocoumarins has been established via rhodium(III)-catalyzed C-H bond activation and intramolecular C-C cascade annulation of enaminones cyclic 1,3-dicarbonyl compounds. The synthetic protocol features a wide range substrates with high functional group tolerance, mild reaction conditions, the selective cleavage enaminone bond. Notably, compounds can in situ-generate iodonium ylide as carbene precursor prepare polycyclic scaffolds by reacting PhI(OAc)2. application this method useful precursors bioactive skeletons is also exemplified.

Язык: Английский

Процитировано

18

I2-DMSO mediated dual α,β-C(sp2)–H functionalization/bicyclization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromone derivatives: chromeno[2,3-b]pyrrol-4(1H)-ones DOI

Shuang‐Gui Lei,

You Zhou, Li‐Sheng Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4843 - 4847

Опубликована: Янв. 1, 2023

An unprecedented dual α,β-C(sp 2 )–H functionalization/bicyclization strategy of o -hydroxyphenyl enaminones for the preparation chromeno[2,3- b ]pyrrol-4(1 H )-ones has been established.

Язык: Английский

Процитировано

18