Manganese‐ Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone methides: Facile Access to β,β‐Diarylmethine Isoxazolines DOI Open Access

Vijay Vara,

Kishor R. Thete,

Ganesh S. Ghotekar

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 9, 2024

A simple and efficient strategy for the synthesis of structurally diverse β,β-diarylmethine substituted isoxazoline derivatives have been developed. This approach employs a manganese-promoted oxidative cyclization coupled with 1,6-conjugate addition unsaturated oximes to p-quinone methides. The key features this study include formation C-O C-C bonds through intramolecular intermolecular interactions, facilitated by in situ generated iminoxyl radicals. isoxazolines, bearing wide range functional groups, were isolated high yields.

Язык: Английский

Photochemical Povarov-type Reactions: Electron Donor–Acceptor Photoactivation by Visible Light DOI Open Access

Meiqiong Tang,

Felicity Draper,

Le Nhan Pham

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2683 - 2690

Опубликована: Фев. 5, 2024

This report investigates the mechanism of photochemical Povarov-type reactions

Язык: Английский

Процитировано

9

EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors DOI
Shupeng Zhang, Dawei Guo,

Mei-Ling Yang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10614 - 10623

Опубликована: Июль 25, 2024

A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis fluorine-containing tetralones quinazolinones. In this transformation, persulfates as electron donors difluoro bromamide acceptors generate complex. This is a promising photochemical method advantages such mild conditions, simple operation, being metal-free, excellent functional group tolerance.

Язык: Английский

Процитировано

7

Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals DOI

Padmanava Barik,

Subhra Sriharsa Behera,

Santosh K. Nanda

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(6)

Опубликована: Апрель 18, 2024

Abstract Electron‐donor acceptor (EDA) complex has been an integral part of visible‐light photocatalysis and is different from the traditional photoredox catalysis, which requires exogenous photocatalyst, typically a colored compound to initiate photocatalytic cycle. Interestingly, EDA‐complex photochemistry found profound use in activating inert α‐C−H bonds amines. The strategy relied upon formation between donor (amine) (Lewis acid), harvesting light energy perform SET process generate radical cation anion intermediates. then loses activated acidic proton (because SET, acidity α‐proton increases by lowering BDE) form α‐amino radical, participates various C−C coupling cascades. In this review, conceptual approaches for generation radicals their bond‐forming reaction under triggered will be discussed with particular emphasis on mechanism 2018 onwards.

Язык: Английский

Процитировано

5

Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts DOI

Sudip Sau,

Shinobu Takizawa, Hun Young Kim

и другие.

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8821 - 8826

Опубликована: Окт. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Язык: Английский

Процитировано

5

Visible‐light Induced C‐3 Carbamoylation of Quinoxalinones Assisted by EDA Complex DOI

Aznur Azim,

Tanumoy Mandal,

Vidhul Vasudevan

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июнь 13, 2024

Abstract A visible‐light‐promoted strategy for the decarboxylative C‐3 carbamoylation of quinoxalinone scaffolds is developed. This approach initiates through formation an EDA complex between oxamic acid and quinoxalinone. Successive SET construct C−C bond. method utilizes aerial oxygen as green oxidant eradicates process from use external photocatalysts transition metals. Detailed synthetic photophysical studies enlighten reaction pathway.

Язык: Английский

Процитировано

4

Electron Donor-Acceptor (EDA) Complex-Driven Activation of N-α C—H Bonds DOI

Junfeng Yang,

Yanqiu Zhao,

Lei Shi

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 559 - 559

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Recent Advances in Photo-promoted Generalized C3-H Alkylation of Quinoxalin-2(1H)-ones DOI
Youpeng Zuo, Xu Bai, Cong Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Recent advances in the photo-promoted C3–H alkylation reaction of quinoxalin-2(1 H )-ones with different agents.

Язык: Английский

Процитировано

0

Photo-induced aerobic cross-coupling of quinoxalin-2(1H)-ones with electron-rich thiophenes DOI
Wei Huang, Tong Wang, Shuying Chen

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Herein, an efficient aerobic cross-coupling of quinoxazolines with electron-rich thiophenes was presented. It's easy and effective access to 3-thiophenyl quinoxalinones without external photo-catalyst or transition-metal catalyst.

Язык: Английский

Процитировано

0

Visible‐Light Mediated C‐3 Amination of Quinoxalin‐ 2(1H)‐ones via Electron Donor‐Acceptor Complexation DOI
Devidas A. More,

Parthasarathy Gayathri,

Kishor R. Thete

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(8)

Опубликована: Май 22, 2024

Abstract The formation of carbon‐nitrogen bonds holds paramount importance in the realm synthetic organic chemistry, finding extensive applications synthesis pharmaceuticals, agrochemicals, and materials. Herein, we describe a novel EDA complex mediated, metal‐ photocatalyst‐free, visible‐light‐initiated direct C‐3 amination biologically important, quinoxalin‐2(1 H )‐one moiety. key to success lies photoactivated electron donor‐acceptor between amine, which undergo subsequent transfer reaction effect desired transformation. A diverse array 3‐aminoquinoxalin‐2(1 )‐ones were prepared employing this process yields are up 87%. This work represents significant advancement toward more environmentally friendly efficient approach, characterized by mild conditions high atom economy.

Язык: Английский

Процитировано

1

Convergent Paired Electrolysis for [3+2] Cycloaddition of Azidotrimethylsilane with N‐Heterocycles DOI

Abhijit Bankura,

Subhadeep Ghosh, Sumit Biswas

и другие.

ChemSusChem, Год журнала: 2024, Номер 17(21)

Опубликована: Май 27, 2024

Abstract A widely used method to obtain tetrazoles is through the azide and nitrile [3+2] cycloaddition. However, this process often involves using non‐recyclable transition metals or Lewis acid catalysts stoichiometric amounts of oxidants additives, which reduces atom efficiency. We have discovered a convergent paired electrochemical reaction perform cycloaddition reaction, without need for metal oxidants. This tetrazolation strategy uses azidotrimethylsilane (TMSN 3 ) N ‐heterocycles in an undivided cell at constant current. use mixture CH CN equivalent H 2 O as co‐solvent room temperature. It crucial produce amount active hydroxyl ions cathodic reduction water. Cyclic voltammetry (CV) studies control experiments confirm that specific electrode electron transfer process, eliminating mediator shuttle electrons. metal‐ oxidant‐free highly compatible with different functional groups produces products moderate good yields. successfully tetrazolated bioactive compounds late stage, scaled up batches efficiently, synthesized free amino‐containing via denitrogenation tetrazoles.

Язык: Английский

Процитировано

1