Cited by Benzoyl cyanide, a general radical acylating reagent for photoredox-catalyzed benzylic site-selective acylation reactions

N-heterocyclic carbene and photocatalyst-catalyzed rapid access to indole ketones via radical C(sp³)–H acylation DOI

Guihua Nie,

Ting Tu,

Tianhui Liao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5397 - 5408

Published: Jan. 1, 2024

Carbene and photocatalyst-catalyzed rapid access to indole ketones via radical C(sp 3 )–H acylation.

Language: Английский

Citations

NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes DOI

Zhaoyang Zhang, Jiayi Yang,

Shihao Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed.

Language: Английский

Citations

Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview DOI

Yujin Jung,

Yoonho Lee, Kwangmin Shin

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 1, 2024

Abstract Acyl fluorides, carbamoyl fluorides and fluoroformates have been employed as efficient reagents in a number of organic syntheses. Their application catalytic transformations, however, began to be explored the early 2000s. Recently, these increasingly gained attention owing their unique reactivity diverse systems. This review aims overview advancements development processes, including transition‐metal catalysis, organocatalysis, cooperative NHC/photoredox where organofluorine compounds are acyl, carbamoyl, ester group donors.

Language: Английский

Citations

Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis DOI

Jiuli Xia,

Yunliang Guo,

Zhiguang Lv

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 790 - 790

Published: Feb. 8, 2024

Monofluoromethyl (CH2F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH2F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In study, we report on visible light-mediated three-component monofluoromethylation/acylation styrene derivatives employing NHC organic photocatalyst dual catalysis. A diverse array α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance selectivity. mild CH2F generation from NaSO2CFH2 holds potential for further applications fluoroalkyl chemistry.

Language: Английский

Citations

Photoredox catalytic deoxygenative divergent functionalizations of alcohols assisted by N,O-heterocyclic carbenes DOI

Qiuzhu Wang,

Youye Tian,

Dan Han

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3471 - 3477

Published: Jan. 1, 2024

A photoredox catalytic deoxygenative platform utilizing readily available alcohols was established, providing an operationally simple and practical route to divergent functionalizations assisted by N,O-heterocyclic carbenes.

Language: Английский

Citations

Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI

Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Citations

Photoinduced Electron Transfer from Xanthates to Acyl Azoliums: Divergent Ketone Synthesis via N‐Heterocyclic Carbene Catalysis DOI

Chang‐Yin Tan, Minseok Kim, Sungwoo Hong

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(32)

Published: June 12, 2023

Abstract Considering the prevalence of alcohols and carboxylic acids, their fragment cross‐coupling reactions could hold significant implications in organic synthesis. Herein, we report a versatile method for synthesizing diverse range ketones from acid derivatives via N ‐heterocyclic carbene (NHC) catalysis. Mechanistic investigations revealed that photoexcited xanthates acyl azoliums undergo single electron transfer (SET) under photocatalyst‐free conditions, generating NHC‐derived ketyl radicals alkyl radicals. These open‐shell intermediates subsequently radical‐radical reaction, yielding valuable ketones. Furthermore, this approach can be employed three‐component involving alkenes enynes, resulting structurally cross‐coupled The unified strategy offers unique opportunity coupling derivatives, accommodating functional groups even complex settings.

Language: Английский

Citations

Radical Deoxygenative Three-Component Reaction of Alcohols, Aryl Alkenes, and Cyanopyridines DOI

Li-Min Feng,

Shuai Liu,

Yuan‐Hong Tu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6225 - 6229

Published: July 15, 2024

We report herein a deoxygenative radical multicomponent reaction involving alcohols, aryl alkenes, and cyanopyridine under photoredox conditions. This method is photoredox-neutral, suitable for late-stage modification, compatible with wide array of alcohols as alkyl sources, including primary, secondary, tertiary alcohols. comprises relay mechanism encompassing the Giese addition alkenes by radicals, followed decyanative pyridination benzyl radicals.

Language: Английский

Citations

Cooperative NHC/Photoredox Catalysis: Three‐Component Reaction of Aroyl Fluorides, Styrenes and Oxalates DOI

Lin Zheng,

Guanghui Lv,

Jianghong Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(5), P. 511 - 515

Published: Nov. 2, 2023

Comprehensive Summary Cooperative NHC/photoredox catalysis has emerged as an important research field in recent years. Herein, this article describes the use of cesium salt derivatives tert ‐alcohols alkyl radical precursors a three‐component reaction with styrene and aromatic acyl fluorides to synthesize α ‐arylalkyl aryl ketones. The aroyl fluoride reacts NHC catalyst, leading formation azolium ion. This ion can then be reduced by photoredox generating corresponding ketyl anion. C‐radical generated from oxalate oxidation undergoes addition derivative, followed cross‐coupling ketone radical, which is fragmented give target ketone.

Language: Английский

Citations

Cooperative Carbene Photocatalysis for B-Amino Ester Synthesis DOI

Nao Tanaka,

Josh Zhu,

Oniya L. Valencia

et al.

Published: Sept. 11, 2023

B-Amino acids are useful building blocks of bioactive molecules, including peptidomimetics and pharmaceutical compounds. The current limited accessibility to B-2,2-type amino which bear an a-quaternary center has their use in chemical synthesis biological investigations. Disclosed herein is the development a new N-heterocyclic carbene/photocatalyzed aminocarboxylation olefins, affording B-2,2-amino esters with high regioselectivity. generation nitrogen-centered radicals derived from simple imides via se-quence deprotonation single-electron oxidation allows for subsequent addition gem-disubstituted olefins regioselectively. intermediate tertiary then cross-couple stabilized azolium-based radical generated situ efficiently construct quaternary centers. Mechanistic studies Stern-Volmer fluorescence quenching experiments support proposed catalytic cycle.

Language: Английский

Citations