Metal–Organic Framework-Encapsulated Anthraquinone for Efficient Photocatalytic Hydrogen Atom Transfer DOI
Zhonghe Wang, Le Zeng, Cheng He

и другие.

ACS Applied Materials & Interfaces, Год журнала: 2022, Номер 14(6), С. 7980 - 7989

Опубликована: Фев. 4, 2022

Anthraquinone (AQ) as an effective hydrogen atom transfer catalyst was limited in photocatalysis application due to the dimerization of reduced AQ. Sr-NDI@AQ, encapsulating AQ into channel Sr-NDI, paved a new way for solving problem and improving catalytic efficiency owing fast electron from ligand through host-guest interaction. The structure Sr-NDI@AQ determined by single-crystal X-ray diffraction, value distance torsion angle between calculated. photochemical electrochemical properties were characterized series experiments. coupling reaction aldehyde phenyl vinyl sulfone photoacetalization carried out, displaying compared Sr-NDI mechanisms proposed radical capture paramagnetic resonance

Язык: Английский

NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones DOI Creative Commons
Lihong V. Wang,

Ruiyang Ma,

Jiaqiong Sun

и другие.

Chemical Science, Год журнала: 2022, Номер 13(11), С. 3169 - 3175

Опубликована: Янв. 1, 2022

The modulation of selectivity highly reactive carbon radical cross-coupling for the construction C-C bonds represents a challenging task in organic chemistry. N-Heterocyclic carbene (NHC) catalyzed transformations have opened new avenue acyl With this method, selective an with alkyl efficient was successfully realized. However, reaction radicals vinyl has been much less investigated. We herein describe NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation 1,3-enynes, providing structurally diversified valuable tetrasubstituted allenyl ketones. Mechanistic studies indicated that ketyl are formed from aroyl fluorides via oxidative quenching photocatalyst excited state, generated chemo-specific sulfonyl addition to finally, key provides

Язык: Английский

Процитировано

74

Organoelectrophotocatalytic Generation of Acyl Radicals from Formamides and Aldehydes: Access to Acylated 3-CF3-2-Oxindoles DOI
Hong He,

Qinhui Wan,

Zhong‐Wei Hou

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7014 - 7019

Опубликована: Сен. 18, 2023

Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as catalyst hydrogen atom transfer (HAT) reagent, which avoids the use an external HAT metal oxidant. A variety have obtained in satisfactory yields CF3-substituted N-arylacrylamides via tandem radical cyclization.

Язык: Английский

Процитировано

49

Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes DOI
Zhiyang Zhang,

Fukun Cheng,

Xinyu Ma

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(12), С. 7331 - 7336

Опубликована: Янв. 1, 2024

A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Язык: Английский

Процитировано

22

Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions DOI
Hong Yu, Jun Xu, Chen An

и другие.

Organic Letters, Год журнала: 2025, Номер 27(10), С. 2526 - 2531

Опубликована: Март 5, 2025

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature our study is ability to perform both using different types The reaction system highly compatible a range aldehydes, yielding C3-esterified C3-alkylated products in moderate-to-good yields. applicability this approach further enhanced by its scalability through continuous-flow synthesis, late-stage modification significant molecules, product derivatization. Our mechanistic investigations reveal radical relay mechanism, triggered hydrogen atom transfer process.

Язык: Английский

Процитировано

4

Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents DOI Creative Commons
Jianming Yan,

Haidi Tang,

Eugene Jun Rong Kuek

и другие.

Nature Communications, Год журнала: 2021, Номер 12(1)

Опубликована: Дек. 10, 2021

Abstract While aldehydes represent a classic class of electrophilic synthons, the corresponding acyl radicals are inherently nucleophilic, which exhibits umpolung reactivity. Generation typically requires noble metal catalysts or excess oxidants to be added. Herein, we report convenient and green approach access radicals, capitalizing on neutral eosin Y-enabled hydrogen atom transfer (HAT) photocatalysis with aldehydes. The generated underwent SOMOphilic substitutions various functionalized sulfones (X–SO 2 R’) deliver value-added products. merger Y sulfone-based SOMOphiles provides versatile platform for wide array aldehydic C–H functionalizations, including fluoromethylthiolation, arylthiolation, alkynylation, alkenylation azidation. present protocol features characteristics, such as being free metals, harmful additives; step-economic; redox-neutral; amenable scale-up assisted by continuous-flow technology.

Язык: Английский

Процитировано

61

Iron(III)-Light-Induced Homolysis: A Dual Photocatalytic Approach for the Hydroacylation of Alkenes Using Acyl Radicals via Direct HAT from Aldehydes DOI
Anurag Chinchole, Marco A. Henríquez, Diego Cortés‐Arriagada

и другие.

ACS Catalysis, Год журнала: 2022, Номер 12(21), С. 13549 - 13554

Опубликована: Окт. 20, 2022

A dual photocatalytic protocol was developed to generate acyl radicals from readily available aldehydes via hydrogen atom transfer (HAT). Synergistic cooperation, being supported by DFT studies, between earth-abundant iron(III)chloride and 9,10-diphenylanthracene (DPA) activate the aldehyde for a HAT step proved be an efficient, economic, green route hydroacylation of electron-deficient alkenes under UV-light irradiation with broad functional group compatibility. This methodology can conveniently scaled up applied produce valuable materials renewable feedstock chemicals.

Язык: Английский

Процитировано

54

Oxidative Radical NHC Catalysis: Divergent Difunctionalization of Olefins through Intermolecular Hydrogen Atom Transfer DOI
Qing‐Zhu Li, Yanqing Liu,

Xin‐Xin Kou

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(44)

Опубликована: Сен. 9, 2022

Oxidative N-heterocyclic carbene (NHC) organocatalysis, typically leading to the formation of acyl azolium reactive intermediates, constitutes one most important activation strategies for NHC-catalyzed chemical transformations. Here, we report an unprecedented oxidative radical NHC catalysis by using peroxyester as external single-electron oxidant realize divergent difunctionalization olefins. The key success this chemistry is catalytic generation oxygen radicals that could trigger intermolecular hydrogen atom transfer activate inert C-H bonds, thereby enabling productive relay process. With protocol, commonly used general chemicals serve precursors allow efficient synthesis value-added products in a straightforward and cost-effective manner. Preliminary mechanistic investigations, including control experiments DFT calculations, shed light on organocatalytic reaction mechanism.

Язык: Английский

Процитировано

53

Efficient access to β-amino acid ester/β-amino ketone derivatives via photocatalytic radical alkoxycabonylimidation/carbonylimidation of alkenes DOI
Peng‐Ju Xia, Fu Liu, Ying‐Ming Pan

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(9), С. 2522 - 2528

Опубликована: Янв. 1, 2022

A photocatalytic protocol for the synthesis of β-amino acid ester and ketone derivatives is developed using simple easy-to-synthesize oxime oxalate phenylglyoxylate as difunctionalization reagents.

Язык: Английский

Процитировано

43

Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds DOI
Jiaqiong Sun, Lihong V. Wang, Guangfan Zheng

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4488 - 4515

Опубликована: Янв. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Язык: Английский

Процитировано

31

New-generation ketoxime ester-type photoinitiator model molecules: Improving photoactivity by introducing o-allyloxy group DOI
Wen Liao,

Ming Jin

Progress in Organic Coatings, Год журнала: 2024, Номер 189, С. 108290 - 108290

Опубликована: Янв. 31, 2024

Язык: Английский

Процитировано

8