BF2‐Chelates of N‐Acylhydrazones as Versatile Coupling Partners in Photoredox Promoted Reactions DOI

Zakhar M. Rubanov,

Vyacheslav I. Supranovich, Vitalij V. Levin

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(22)

Published: May 3, 2023

Abstract Five‐membered difluoroboryl chelate complexes are competent substrates for radical reactions with various precursors including potassium trifluoroborates, bis(catecholato)siliconates, 4‐alkyl‐substituted Hantzsch esters, dihydroquinazolinones, esters of N ‐hydroxyphthalimide, Katritzky salts, alkyl iodides and thiols. Using these reagents, primary, secondary, tertiary radicals can be generated under oxidative or reductive conditions add at the C=N bond chelates leading to hydrazide products.

Language: Английский

Carbon–sulfur bond formation via photochemical strategies: An efficient method for the synthesis of sulfur-containing compounds DOI
Daoshan Yang,

Qiuli Yan,

Enjie Zhu

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(4), P. 1798 - 1816

Published: Sept. 27, 2021

Language: Английский

Citations

134

Sulfonium Salts as Acceptors in Electron Donor‐Acceptor Complexes DOI Creative Commons
Leendert van Dalsen,

Rachel E. Brown,

James A. Rossi‐Ashton

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(29)

Published: March 24, 2023

Abstract The photoactivation of electron donor‐acceptor complexes has emerged as a sustainable, selective and versatile strategy for the generation radical species. Electron (EDA) complexation, however, imposes electronic constraints on donor acceptor components this can limit range radicals that be generated using approach. New EDA complexation strategies exploiting sulfonium salts allow to from native functionality. For example, aryl salts, formed by activation arenes, serve in due their electron‐deficient nature. This “sulfonium tag” approach relaxes parent substrate dramatically expands complexation. In review, these new applications will introduced areas chemical space rendered accessible through innovation highlighted.

Language: Английский

Citations

96

Visible light-induced Z-scheme V2O5/g-C3N4 heterojunction catalyzed cascade reaction of unactivated alkenes DOI
Qingwen Gui, Fan Teng, Peng Yu

et al.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2022, Volume and Issue: 44, P. 111 - 116

Published: Dec. 2, 2022

Language: Английский

Citations

80

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics DOI

Fukun Cheng,

Lulu Fan, Qi‐Yan Lv

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7971 - 7977

Published: Jan. 1, 2023

Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C–H alkylation of N -heteroaromatics.

Language: Английский

Citations

48

Photosynthesis of 3-Alkylated Coumarins from Carboxylic Acids Catalyzed by a Na2S-Based Electron Donor–Acceptor Complex DOI

Hai‐Yang Song,

Meiyi Liu,

Jing Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2288 - 2295

Published: Feb. 4, 2023

A simple and practical electron donor-acceptor (EDA) strategy to synthesize various 3-alkylated coumarins from easily available naturally abundant carboxylic acids under photocatalyst-, oxidant-, additive-free mild conditions is reported. Using Na2S as the catalytic donor, a series of primary, secondary, tertiary carbon radicals can be efficiently generated, EDA complex regenerated without an alkaline additive.

Language: Английский

Citations

31

Photocatalytic Sulfonylation: Innovations and Applications DOI
Anxiang Huang,

Rui Li,

Qi‐Yan Lv

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

Citations

10

Visible‐Light‐Promoted Electron Donor‐Acceptor Complex Enabled Decarboxylative Alkylation of Quinoxalin‐2(1H)‐ones and N‐Hydroxyphthalimide Esters with Na2S as a Catalytic Donor DOI

Hai‐Yang Song,

Zhuo‐Tao Zhang,

Hong‐Yu Tan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(2)

Published: Jan. 11, 2023

Abstract We developed a novel and efficient method for the synthesis of various 3‐alkylated quinoxalin‐2(1 H )‐ones (32 examples, 70%–96% yields) through electron donor‐acceptor complex enabled alkylation with N ‐ hydroxyphthalimide esters as alkyl source Na 2 S catalytic donor under external photocatalyst‐, oxidant‐ additive‐free conditions.

Language: Английский

Citations

22

Recent advances in the photocatalytic synthesis of aldehydes DOI
Yi Wang, Xiaofei Liu, Wei‐Min He

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(16), P. 4198 - 4210

Published: Jan. 1, 2023

This review summarizes the recently developed photocatalytic strategies for installation of formyl group into various scaffolds.

Language: Английский

Citations

19

Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis DOI

Guiqing Xu,

Jiayuan Lv,

Qingjie Ding

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2777 - 2781

Published: Feb. 5, 2024

2,1,3-Benzothiadiazole is widely used as a privileged scaffold in pharmaceuticals and organic functional materials. Nonetheless, many current methods for the functionalization of 2,1,3-benzothiadiazole rely on preactivation, transition metal catalysts/promoters, or an elevated reaction temperature. Herein we disclose transition-metal-free visible-light-induced photocatalytic method direct C–H alkylation using readily accessible carboxylic acid derivatives, i.e., N-hydroxyphthalimide esters (NHPEs), alkylating reagents under room This mild scalable highlighted by late-stage installation benzothiadiazole drugs natural products.

Language: Английский

Citations

8

Dual Acridine/Decatungstate Photocatalysis for the Decarboxylative Radical Addition of Carboxylic Acids to Azomethines DOI

Zakhar M. Rubanov,

Vitalij V. Levin, Alexander D. Dilman

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3174 - 3178

Published: April 8, 2024

A concept for the dual use of acridine and tetrabutylammonium decatungstate photocatalysts in reactions carboxylic acids is proposed. Imines generated situ from aldehydes p-methoxyaniline, as well other azomethines, were used radical acceptors. The role believed to facilitate turnover photocatalyst by means hydrogen atom transfer.

Language: Английский

Citations

8