Recent Advances in Radical Reactions of 1,n‐Enynes with Phosphorus‐Centered Radicals DOI

Hairui Ni,

Siyan Fan,

Tongyan Yu

и другие.

ChemistrySelect, Год журнала: 2024, Номер 9(42)

Опубликована: Ноя. 1, 2024

Abstract Organophosphorus compounds have been widely used as achiral and chiral ligands in organic synthesis (PPh 3 , BINAP, dppe, Duphos, Xantphos, PPFA, Chiraphos, SEGPHOS), flame retardants, functional materials (LED, PV), well agrochemicals medicines due to their broad biological activities. As the privileged versatile building blocks, 1,n‐enynes successfully applied of various functionalized cyclic based on two active unsaturated chemical bonds (C═C double C≡C triple bonds). With development highly selective efficient methods chemistry, organophosphorus through radical cascade strategy has attracted considerable attention recent years. In here, we summarized main achievements reactions with phosphorus‐centered radicals. Furthermore, also displayed detailed reaction mechanisms this review.

Язык: Английский

Cu-Catalyzed Relay Functionalization of Alkenes: Diverse Synthesis of Diazidated Quinazolinones and Polycyclic Imidazoles DOI

Ji-Ming Xi,

Zhonglin Wei, Wei‐Wei Liao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp3)–H functionalization alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were prepared good yields a broad substrate scope. Moreover, direct azidation α-C(sp3)–H bond corresponding N-heterocycles has been demonstrated on basis mechanistic studies, provide alternative late-stage approach derivatization N-heterocyclic scaffolds.

Язык: Английский

Процитировано

1

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(18), С. 2556 - 2559

Опубликована: Янв. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Язык: Английский

Процитировано

5

Photo-induced phosphorylation/cyclization of N-homoallyl and N-allyl aldehyde hydrazones to access phosphorylated tetrahydropyridazines and dihydropyrazoles DOI

Ling-Li Liu,

Yechun Wu,

Chengli Xiang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(35), С. 4687 - 4690

Опубликована: Янв. 1, 2024

A visible-light-induced carbophosphorylation/cyclization of N -homoallyl and -allyl aldehyde hydrazones with phosphine oxides was developed to obtain phosphorylated tetrahydropyridazines dihydropyrazoles.

Язык: Английский

Процитировано

5

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

и другие.

ACS Omega, Год журнала: 2024, Номер 9(26), С. 28129 - 28143

Опубликована: Июнь 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Язык: Английский

Процитировано

5

Electrochemical Trifluoromethylation/Bicyclization of N-Cyanamide Alkenes: Synthesis of Bicyclic Amidine Derivatives DOI

Zhi-Hua Yan,

Yan Yan, Zhonglin Wei

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2718 - 2725

Опубликована: Фев. 2, 2024

An anodically oxidizing trifluoromethylation cascade of N-cyanamide alkene bearing two electronically differentiated olefin moieties was reported, in which various N-unsaturated acyl cyanamide alkenes and CF3SO2Na acting as readily available starting materials furnished nonaromatic fused azaheterobicyclic compounds a highly efficient sustainable manner. The broad substrate scope, facile scalability, sustainability enabled this electrochemical process to be an appealing complement for trifluoromethylated cyclic amidines.

Язык: Английский

Процитировано

4

Visible-light-induced photocatalyst-free cascade cyclization of 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Lili Wang,

Yuxin Luo

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(56), С. 7228 - 7231

Опубликована: Янв. 1, 2024

A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.

Язык: Английский

Процитировано

4

Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles DOI

Yechun Wu,

Han Liu,

Lingli Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(35), С. 7079 - 7084

Опубликована: Янв. 1, 2023

Polychloromethylative cyclization of N-alkenyl indoles was developed under metal-free conditions to afford tricyclic pyridoindolones and pyrroloindolones in moderate good yields. In the reaction, commercially available CHCl3 CH2Cl2 were employed as tri- dichloromethyl radical sources. Moreover, dichloromethylated polycyclic benzoimidazoles can also be obtained standard conditions.

Язык: Английский

Процитировано

9

Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CF2-substituted ring-fused imidazoles DOI Creative Commons
Hui-Nan Wang, Shaohui Lin, Hui Hong

и другие.

RSC Advances, Год журнала: 2025, Номер 15(16), С. 12739 - 12745

Опубликована: Янв. 1, 2025

A mild and effective visible-light-induced decarboxylative radical cascade reaction of olefin-containing imidazoles α-fluorinated carboxylic acids, has been developed to afford monofluoromethylated or aryldifluoromethylated polycyclic imidazoles.

Язык: Английский

Процитировано

0

Polychloromethylation‐Initiated Radical 1,2‐Aryl Migration of α,α‐Diarylallyl Alcohols via Visible‐Light Photoredox Catalysis DOI

Xian Wu,

Chengli Xiang,

Jin‐Tao Yu

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(31)

Опубликована: Июнь 15, 2023

Abstract A visible‐light induced radical 1,2‐aryl migration of α,α‐diarylallyl alcohols was developed under mild and metal‐free conditions. Commercially available CHCl 3 CH 2 Cl were used as tri‐ dichloromethyl precursors. Structurally diverse β‐polochloromethylated ketones obtained in good to moderate yields via neophyl‐type rearrangement. Besides, the polychloromethyl group can be easily transformed into other useful functional groups.

Язык: Английский

Процитировано

8

Visible-Light-Promoted Radical Cascade Cyclization of 2-Vinyl Benzimidazoles: Access to Benzo[4,5]imidazo[1,2-b]isoquinolin- 11(6H)-ones DOI

Yao-Tian Wang,

Mai Zhang, Zhixing Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7770 - 7779

Опубликована: Май 13, 2024

A visible-light-enabled photoredox radical cascade cyclization of 2-vinyl benzimidazole derivatives is developed. This chemistry applicable to a wide range

Язык: Английский

Процитировано

2