A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions DOI

Monika,

Chander Chander,

Sita Ram

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 12(1)

Published: Nov. 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.

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

148

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

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2356 - 2369

Published: Jan. 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.

Language: Английский

Citations

78

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

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6062 - 6066

Published: Aug. 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.

Language: Английский

Citations

64

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

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(3), P. 512 - 516

Published: Jan. 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.

Language: Английский

Citations

50

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

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(13), P. 5058 - 5063

Published: Jan. 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.

Language: Английский

Citations

64

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

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(16), P. 4416 - 4420

Published: Jan. 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.

Language: Английский

Citations

39

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

Liyun Zhou,

Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 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.

Language: Английский

Citations

32

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

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

Citations

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

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4833 - 4838

Published: March 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.

Language: Английский

Citations

23

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

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(10), P. 6562 - 6572

Published: April 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.

Language: Английский

Citations

30