Metal‐Free and Visible Light‐Induced Difunctionalizations of α‐CF3 Styrenes with Aryl Diazonium Salts and Hetero Nucleophiles DOI
Lu Zhang, Shuai Liu, Mingming Ma

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Сен. 5, 2023

Abstract Metal‐free, visible light‐induced difunctionalizations of α ‐CF 3 styrenes with aryl diazonium salts and various hetero nucleophiles (ROH, H 2 O, N − F ) are described. This concise protocol provided easy access to the tertiary alkyl ethers, alcohol fluorides good yields excellent functional group tolerance. In addition, four‐component “SO ” insertion reaction also worked efficiently produce , β ‐sulfonyl ethers in moderate yields. A radical‐polar crossover coupling pathway was proposed for C−O bond formation.

Язык: Английский

Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions DOI
Peng Zhao, Lingfeng Wang,

Xiaoshuang Guo

и другие.

Organic Letters, Год журнала: 2023, Номер 25(18), С. 3314 - 3318

Опубликована: Май 1, 2023

We disclose herein an efficient photochemical formal [3+2+1] annulation strategy for the transformation of diazocarbonyl compounds into various fluorinated nitrogen-containing heterocycles. This is characterized by reacting fluoroalkyl radicals with α-diazoketones, which are used as infrequent denitrogenated synthons under visible light. Moreover, a wide range N-heterocycles containing precious CF3 and perfluoroalkylated groups constructed in moderate to good yields. Notably, this may provide fruitful path synthesis complex organofluorides via diazo/fluorine/radical chemistry.

Язык: Английский

Процитировано

39

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

Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes DOI Creative Commons
Tong Zhang, Jabor Rabeah, Shoubhik Das

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 18, 2024

Abstract Controlling regioselectivity during difunctionalization of alkenes remains a significant challenge, particularly when the installation both functional groups involves radical processes. In this aspect, methodologies to install trifluoromethane (−CF 3 ) via have been explored, due importance moiety in pharmaceutical sectors; however, these existing reports are limited, most which affording only corresponding β-trifluoromethylated products. The main reason for limitation arises from fact that −CF group served as an initiator those reactions and predominantly preferred be installed at terminal (β) position alkene. On contrary, functionalization internal (α) would provide valuable products, but meticulous approach is necessary win switch. Intrigued by we here develop efficient regioselective strategy where α-position Molecular complexity achieved simultaneous insertion sulfonyl fragment (−SO 2 R) β-position. A precisely regulated sequence generation using red light-mediated photocatalysis facilitates switch position. Furthermore, demonstrates broad substrate scope industrial potential synthesis pharmaceuticals under mild reaction conditions.

Язык: Английский

Процитировано

8

Rongalite as a Versatile Reagent in Organic Synthesis DOI Open Access
Huai‐Yu Wang, Xiang‐Long Chen, Yan‐Dong Wu

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(23), С. 3388 - 3400

Опубликована: Июнь 24, 2023

Comprehensive Summary This review provides a comprehensive summary of progress to date in the utilization rongalite as versatile reagent organic synthesis, with focus on recent researches. The contents have been organized according functions exhibited by rongalite. Reaction mechanisms are provided, demonstrating multifaceted roles this compound various transformations, including sulfone, C1 or masked proton source and single electron donor reducing agent.

Язык: Английский

Процитировано

17

Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite DOI
Xiang‐Long Chen, Chun‐Yan Wu, Dong‐Sheng Yang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(12), С. 1360 - 1366

Опубликована: Фев. 23, 2024

Comprehensive Summary The conversion of CF 3 ‐alkenes to gem ‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use green and readily available reducing salt mediate these reactions remains be explored. In this work, a concise construction gem‐ difluoroalkenes, which requires neither catalyst nor metal agent, was established. Rongalite, safe inexpensive industrial product, employed as both radical initiator reductant. This procedure compatible with linear cyclic diaryliodonium salts, enabling wide variety substrates (>70 examples). utility approach demonstrated through gram‐scale synthesis efficient late‐stage functionalizations anti‐inflammatory drugs.

Язык: Английский

Процитировано

5

Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4214 - 4218

Опубликована: Янв. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Язык: Английский

Процитировано

5

Reductive N-Formylation of Nitroarenes Mediated by Rongalite DOI
Huai‐Yu Wang, Xiang‐Long Chen, Chun‐Yan Wu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7220 - 7224

Опубликована: Сен. 28, 2023

Herein, we disclose a straightforward approach to access transition-metal-free reductive N-formylation of nitroarenes. This reaction integrates the dual role rongalite, which acts as reductant and C1 building block concurrently. provides an alternative method for synthesis N-aryl formamides from nitroarenes, including construction C–N bond. The utility this protocol was demonstrated by scale-up late-stage functionalizations complex molecules.

Язык: Английский

Процитировано

10

Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates DOI
Suryakant S. Chaudhari, Chandrakant B. Nichinde, Baliram R. Patil

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(8), С. 1727 - 1732

Опубликована: Янв. 1, 2024

In this study, we developed a novel methodology involving base-controlled, rongalite-mediated reductive/aldol reaction, followed by cyclization of isatylidene malononitriles/cyanoacetates, resulting in the synthesis spiro[2,3-dihydrofuran-3,3'-oxindole]. Additionally, have disclosed dimerization process for malononitriles, yielding dispiro[cyclopent-3'-ene]bisoxindole. The utilization rongalite reaction serves dual purpose, acting both as reducing agent and C1 synthon. approach has several advantages like simple setup, wide substrate scope, requiring less time, using water green solvent, no metal or catalyst is required products can be easily isolated

Язык: Английский

Процитировано

4

Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis DOI

Ya-Fei Hu,

Wei Han,

Ye-Kun Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5144 - 5150

Опубликована: Янв. 1, 2024

A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.

Язык: Английский

Процитировано

4

Combining Hydrodefluorination and Defluorophosphorylation for Chemo- and Stereoselective Synthesis of gem-Fluorophosphine Alkenes DOI

Ya‐Fei Hu,

Man-Hang Feng,

Peng‐Yuan Zhang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(34), С. 6368 - 6373

Опубликована: Авг. 18, 2023

A chemo-, regio-, and stereoselective reaction of trifluoromethyl enones, phenylsilane, phosphine oxides through a sequential hydrodefluorination defluorophosphorylation relay is developed for the synthesis distinctive gem-fluorophosphine alkenes. This multicomponent occurred under transition-metal-free conditions with good functional group tolerance. Moreover, preinstalled carbonyl auxiliary important tuning reactivity β-trifluoromethyl thereby enabling controllable selective functionalization two fluorine atoms in trifluoromethylated enones.

Язык: Английский

Процитировано

9