Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes DOI Creative Commons
Michael Jakob, Luca Steiner,

Marius Göbel

и другие.

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 17642 - 17653

Опубликована: Ноя. 15, 2024

The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare handle compounds, alkyl silanes are attractive substrates chemistry desilylative mesolysis the corresponding cations known be rapid. Here, we report successful application benzyl silane derivatives source radicals in dual NHC/photoredox-catalyzed radical–radical coupling acyl fluorides. Relatively electron-rich reacted smoothly afford ketones generally good yields, while optimization NHC photocatalyst allowed a wider scope including primary substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O- S-heteroatoms can also serve sources these

Язык: Английский

Homologation of Ketones: Direct Transformation of Alkyl Ketones to Aryl Ketones via Photoredox Catalyzed Deacylation-Aroylation Sequence DOI
Tian Wang, Zengyu Zhang, Fan Gao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6915 - 6920

Опубликована: Авг. 8, 2024

Ketones, as essential functional group skeletons, have garnered significant interest due to their diverse transformations. Herein, we describe a versatile photoredox catalyzed deacylation-aroylation strategy that enables the direct transformation of alkyl ketones aryl ketones. This process involves deacylation dihydroquinazolinones derived from generate radicals, followed by subsequent NHC-catalyzed or NHC-mediated radical aroylation.

Язык: Английский

Процитировано

10

Photocatalytic C–C bond thio(seleno)esterification of 1,2-diketone-derived pro-aromatic intermediates DOI Creative Commons
Amit Pal, Soumya Sarkar,

Aaron Shibu

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We report an organophotocatalyst-enabled oxidant-free C–S/C–Se bond coupling of (un)symmetrical 1,2-diketones via pro-aromatic dihydroquinazolinones/benzothiazolines, employing readily accessible disulfides/diselenides.

Язык: Английский

Процитировано

1

Photocatalytic C–C Bond Azidation and Cyanation of Acyclic Ketones via a Pro-aromatic Intermediate DOI
Sandip Bag,

Amit Dhibar,

Shruti Moorthy

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 10, 2025

Herein, we report a formal C–C bond azidation and cyanation of unactivated aliphatic ketones using commercially available tosyl azide cyanide, respectively. A visible-light-mediated organophotocatalyst enables radical ketone-derived pro-aromatic dihydroquinazolinones (under mostly redox-neutral conditions) as supported by preliminary mechanistic studies. These metal-free scalable protocols can be used to synthesize tertiary, secondary, primary alkyl azides nitriles with good functional group tolerance postsynthetic diversification the group, including bioconjugation.

Язык: Английский

Процитировано

1

Imidazolium‐dithiocarboxylate zwitterions catalysed ring‐opening additions of cyclopropenones DOI Open Access
Qi Wu, Fang Zhang, Qichao Zhang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Янв. 23, 2025

Abstract Imidazolium‐dithiocarboxylate zwitterions (NHC ⋅ CS 2 ), a novel organocatalyst that derived from N‐heterocyclic carbene (NHC), was used to activate cyclopropenones. Under the catalysis of 10 mol% NHC 2, range phenols, alcohols, primary and secondary amines react with cyclopropenones produce trisubstituted α , β ‐unsaturated esters amides in 46–95% yield. More than 68 products, including 7 natural product derivatives have been synthesized through this method. Mechanism study showed act as Lewis base C=C double bond trigger ring‐opening reaction. HRMS analysis indicated formation key adduct cyclopropenone. importantly, demonstrated completely different catalytic activity catalysts, latter one cannot catalyse these reactions.

Язык: Английский

Процитировано

0

N‐Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells DOI Creative Commons
Yanqing Liu, Leilei Fu,

Liwu Hong

и другие.

Advanced Science, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

Abstract Isoflavonoids represent a privileged scaffold among various bioactive natural products, rendering their structural diversification through green synthesis and subsequent biological evaluations compelling research area. In this study, an NHC organocatalytic radical acylalkylation of 1,3‐enynes using salicylaldehydes is presented, followed by cascade intramolecular annulation, yielding series fluorinated isoflavone derivatives with substantial yields under environmental‐friendly conditions. This approach, distinguished its excellent modularity high functional group tolerance, represents unprecedented 1,3,4‐trifunctionalization designed for the isoflavones in single step. Furthermore, it demonstrated that these synthesized isoflavonoids effectively suppress proliferation breast cancer cells, most potent compound 8 also inhibiting migration MDA‐MB‐231 cells.

Язык: Английский

Процитировано

0

A Radical Precursor Based on the Aromatization of p-Quinol Esters Enabled by Pyridine-Boryl Radical DOI
Xiaoli Huang,

Ruji Xiong,

Yi Cui

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

A class of prearomatic carboxylic acid p-quinol ester radical precursors has been developed successfully, which could undergo homolytic cleavage the para C-O bond esters via pyridine-boryl radical-induced aromatization in presence pyridines and diboron reagents, affording corresponding alkyl decarboxylation from carboxyl situ. In addition, were further applied substitution with phenylsulfonyl compounds self-coulpings. This method not only provides a new approach to generation intermediate but also expands application boron radicals.

Язык: Английский

Процитировано

0

Visible-Light-Induced NHC-Catalyzed Carboacylation Reaction of Alkenes from Aryl Thianthrenium Salts and Aldehydes DOI

Dong-Sheng Ji,

Youwan Ye,

Peiqin Zhang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 21, 2025

A metal-free, visible-light-induced NHC-catalyzed multiple-component reaction involving aldehydes and aryl thianthrenium salts for the carboacylation of alkenes is reported. In this reaction, NHC-activated afforded Breslow intermediates, which reduced generated radicals. The resulting radicals underwent radical addition reactions to yield arylacylation products, in presence iodoalkane, participated halogen atom transfer process generate alkyl facilitate olefin alkylacylation.

Язык: Английский

Процитировано

0

Visible light-mediated 1,3-acylative chlorination of cyclopropanes employing benzoyl chloride as bifunctional reagents in NHC catalysis DOI
Mingrui Li, Song Xiao,

Xueyun Lu

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

Язык: Английский

Процитировано

0

Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction DOI Creative Commons
Xiaotang Chen,

Bao‐Chen Qian

Molecules, Год журнала: 2025, Номер 30(8), С. 1711 - 1711

Опубликована: Апрель 11, 2025

Traditionally employed as hydrogenation reagents, benzothiazolines have emerged versatile carbanion and radical transfer playing a vital role in the construction of various carbon-carbon bonds. The cutting-edge progress photochemistry chemistry prompted study visible light-driven reactions, bringing into vibrant focus. Their chemical processes been uncovered to encompass variety activation mechanisms, with five distinct modes having identified. This work reviews innovative applications donors alkyl or acyl groups, achieving hydroalkylation hydroacylation substitution. By examining their diverse this review highlights potential serving groups for further research development. Moreover, will offer exemplary inspiration synthetic chemists, contributing ongoing evolution utility organic synthesis.

Язык: Английский

Процитировано

0

Visible-Light-Driven Borylacylation of Alkenes by NHC/Photoredox Dual Catalysis: Accessing Boryl 1,4-Dicarbonyl Architectures DOI

Ze‐Le Chen,

S. MA, Shengnan Tang

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7101 - 7111

Опубликована: Апрель 16, 2025

Язык: Английский

Процитировано

0