Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C–H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides DOI
Wenbo Ma,

Yuqiang Tan,

Yang Wang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6200 - 6205

Published: Aug. 2, 2021

Herein, we report a highly efficient ruthenium-catalyzed peri-selective C(sp2)–H acylmethylation of 1-naphthols with α-carbonyl sulfoxonium ylides by utilizing hydroxyl as weakly coordinating directing group. This new method imparts good reactivity, excellent chemo- and regioselectivity, broad functional group tolerance involves mild reaction conditions. The C–H acylmethylated products can be readily cyclized into fluorescent annulated pyrans one-pot process.

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

150

Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes DOI Open Access
Kai Sun, Xin Wang, Chao Li

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(19), P. 3100 - 3119

Published: Jan. 1, 2020

This review highlights recent progress in tandem selenocyclization and tellurocyclization with alkenes alkynes, an emphasis on the scopes, limitations mechanisms of these different reactions.

Language: Английский

Citations

140

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals DOI
Rajib Mandal,

Bholanath Garai,

Basker Sundararaju

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(6), P. 3452 - 3506

Published: March 3, 2022

Transition-metal-catalyzed C–H bond functionalizations have had an enormous influence on organic synthesis in recent times. However, the use of low-abundance 4d and 5d metals is almost inevitable, they are high demand. This will be a cause concern, hence, it important to develop methods based 3d metals, which widely present Earth's crust. In this regard, metal catalysts or their precursors for catalysis, general, functionalizations, particular, has gained significant momentum The major development catalytic with been achieved predominantly strongly coordinating directing groups such as pyridyl, pyrimidinyl, pyrazolyl, 8-amino-quinolinyl groups. Thus, prefunctionalization substrates these necessary, contradicts step- atom-economy activation. commonly available functional aldehyde, ketone, carboxylic acid, amide, hydroxy, N-oxides loosely bind through weak-coordination. These weakly orient activate regioselectively without need preinstalled Although challenging, contemporary topic actively pursued by many researchers Through article, we provide comprehensive overview metal-catalyzed, coordinating, directing-group-enabled reported until March 2021.

Language: Английский

Citations

118

Aminoselenation and Dehydroaromatization of Cyclohexanones with Anilines and Diselenides DOI
Lin Zhao,

Yujie Weng,

Xinyu Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4835 - 4839

Published: May 29, 2024

A three-component cascade reaction involving cyclohexanones, anilines, and diaryl diselenides under metal-free conditions is reported. The ortho-selenation of cyclohexanones with diselenides, followed by sequential dehydroaromatization enables the preparation a variety o-selanyl anilines in moderate to excellent yields. This innovative transformation notable for its tolerance functional groups suitable late-stage modification complex pharmaceuticals.

Language: Английский

Citations

21

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

30

Transition Metal‐Catalysed Direct C−H Bond Functionalizations of 2‐Pyridone Beyond C3‐Selectivity DOI
Aniruddha Biswas, Saurabh Maity,

Subarna Pan

et al.

Chemistry - An Asian Journal, Journal Year: 2020, Volume and Issue: 15(14), P. 2092 - 2109

Published: June 5, 2020

2-Pyridone is a ubiquitous motif in natural products, drug molecules, ligands catalysis and organic materials. There necessity of direct step-economic methods for the construction 2-pyridone based molecules. Strategically, primary developments have led to C3-functionalizations due inherent reactivity this center. Despite this, many elegant transition metal-catalysed been established introduce versatile functional groups at C4, C5 C6-position via C-H bond functionalizations. This minireview focuses on categorized introduction different scaffolds beyond C3-selectivity discusses substrate scope, limitations plausible mechanistic details.

Language: Английский

Citations

53

Direct Electrochemical Selenylation/Cyclization of Alkenes: Access to Functionalized Benzheterocycles DOI
Xiaomei Cheng,

Balati Hasimujiang,

Zhongnan Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(22), P. 16045 - 16058

Published: July 30, 2021

A catalyst-free, environmentally friendly, and efficient electrochemical selenylation/cyclization of alkenes has been developed with moderate to excellent yields. This selenylated transformation proceeds smoothly tolerates a wide range synthetically useful groups deliver diverse functionalized benzheterocycles, including iminoisobenzofuran, lactones, oxindoles, quinolinones. Moreover, the present synthetic route could also be readily scaled up gram quantity convenient operation in an undivided cell.

Language: Английский

Citations

45

Visible Light‐Induced Synthesis of Functionalized Coumarins DOI
Jitender Singh, Anuj Sharma

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(14), P. 3411 - 3438

Published: April 16, 2021

Abstract Functionalized coumarins are privileged scaffolds which display diverse pharmacological and physiological activities, a myriad of applications in medical science biomedical research. Owing to these multifarious activities coumarins, synthetic chemists actively engaged developing new superior methods for their synthesis. In the last decade, synthesis functionalized via visible light‐induced methodologies has turned into one most significant fundamental missions organic This review covers literature on under light‐assisted methodologies. magnified image

Language: Английский

Citations

41

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization DOI
Chang‐Sheng Wang,

Yuan Xu,

Yiliang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4972 - 5027

Published: Jan. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Language: Английский

Citations

20

Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi DOI
Zhongnan Xu,

Jiwen Yao,

Kaihui Zhong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5572 - 5585

Published: April 21, 2023

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling α-keto sulfoxonium ylides with diselenides. The versatility electrochemical manifold enabled selenylation ample scope broad functional group tolerance, as well setting stage for modification complex bioactive Detailed mechanistic studies revealed that key C-Se bond was constructed using n-Bu4NI an electrolyte catalyst electrosynthetic protocol. Finally, desired showed excellent antimicrobial activity against Candida albicans, which can be identified lead further exploration.

Language: Английский

Citations

19