A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions DOI

Monika,

Chander Chander,

Sita Ram

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 12(1)

Опубликована: Ноя. 26, 2022

Abstract In multicomponent reactions, three or more reactants combine in one pot to form a product without the isolation of intermediate and most contribute newly formed reducing number steps involved waste generated. Molecular iodine is mild, efficient, relatively nontoxic, inexpensive, commercially available, catalyzes various organic reactions due its Lewis acidic behaviour. The development catalyzed by molecular indeed good green alternative for synthetic chemistry. aim this article review all important reported since 2013 order envisage some new efficient protocols synthesis structurally complex molecules.

Язык: Английский

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

и другие.

Chemical Reviews, Год журнала: 2022, Номер 122(24), С. 17479 - 17646

Опубликована: Окт. 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

Язык: Английский

Процитировано

155

Recent advances in transition metal-free annulation toward heterocycle diversity based on the C–N bond cleavage of enaminone platform DOI
Xiao Yun Chen, Xiaotong Zhang, Jie‐Ping Wan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(12), С. 2356 - 2369

Опубликована: Янв. 1, 2022

Enaminones and analogous stable enamines are well known as platform building blocks in organic synthesis for the construction of heterocyclic compounds, especially N-heterocycles. To date, enaminones have been successfully employed various 5- or 6- membered heterocycles. Recently, synthetic protocols accomplished by diversity-oriented annulation reactions based on C-N bond cleavage gained notable success. In this review, development transition metal-free product featuring a is reviewed.

Язык: Английский

Процитировано

78

Radical-Polar Crossover Enabled Triple Cleavage of CF2Br2: A Multicomponent Tandem Cyclization to 3-Fluoropyrazoles DOI

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

и другие.

Organic Letters, Год журнала: 2023, Номер 25(32), С. 6062 - 6066

Опубликована: Авг. 8, 2023

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation reactive intermediate gem-difluorovinylimine ion key this transformation. This protocol unlocks reactivity adds significant synthetic values fluorine chemistry.

Язык: Английский

Процитировано

66

A Traceless Heterocyclic Amine Mediator in Regioselectivity−Switchable Formal [1 + 2 + 2] Cycloaddition Reaction to 1,3,4- and 1,4,5-Trisubstituted Pyrazoles DOI
Jie Huo, Xiao Geng, Wanmei Li

и другие.

Organic Letters, Год журнала: 2023, Номер 25(3), С. 512 - 516

Опубликована: Янв. 12, 2023

Switchable multicomponent reactions have been attractive tools for the construction of compound libraries with skeleton diversity and complexity by slightly changing reaction conditions. Described herein is a regioselectivity-switchable formal [1 + 2 2] cycloaddition from difluoroalkyl compounds, enaminones, RNHNH2, ultimately using 1-methylindazol-3-amine as traceless mediator to switch inherent regioselectivity 1,3,4-trisubstituted pyrazole formation 1,4,5-trisubstituted pyrazoles. Remarkable features this work include mild conditions, simple operation, broad scopes.

Язык: Английский

Процитировано

50

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

Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines DOI
Huan Gao,

Liyun Zhou,

Jie‐Ping Wan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7188 - 7198

Опубликована: Май 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Язык: Английский

Процитировано

32

Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones DOI
Leiqing Fu, Jie‐Ping Wan

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

Процитировано

28

Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones DOI

Demao Chen,

Changfeng Wan, Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4833 - 4838

Опубликована: Март 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Язык: Английский

Процитировано

24

I2-Promoted site-selective C–C bond cleavage of aryl methyl ketones as C1 synthons for constructing 5-acyl-1H-pyrazolo[3,4-b]pyridines DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(16), С. 4416 - 4420

Опубликована: Янв. 1, 2022

A novel iodine promoted [1 + 3 2] cleavage cyclization reaction for the synthesis of 1 H -pyrazolo[3,4- b ]pyridines from aryl methyl ketones, 5-aminopyrazoles and enaminones has been established.

Язык: Английский

Процитировано

39

A Straightforward Approach to Fluorinated Pyrimido[1,2-b]indazole Derivatives via Metal/Additive-Free Annulation with Enaminones, 3-Aminoindazoles, and Selectfluor DOI

Zhaoliang Xu,

Xiao Geng,

Yiwen Cai

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(10), С. 6562 - 6572

Опубликована: Апрель 29, 2022

A novel and efficient three-component reaction with two C–N bonds one C–F bond formation has been reported, which provides a straightforward route to variety of fluorinated pyrimido[1,2-b]indazole derivatives. This transformation the advantage excellent functional group compatibility, including aliphatic aromatic substituents enaminones. Moreover, metal additives are not necessary for this reaction, is great significance synthesis application heterocycles.

Язык: Английский

Процитировано

30