Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination DOI
Yongli Zhao,

Dingsheng Cao,

Jie‐Ping Wan

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 29, 2024

Abstract The C3‐alkenylation of indoles have been developed by means a novel in situ iodination tactic which is capable mediating the Heck coupling with alkenes. method features specific site‐selectivity oriented C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well highly general tolerance to different terminal alkenes, including unactivated acrylates, acrylic acid, vinyl sulfone functionalized natural products.

Язык: Английский

Ruthenium‐Catalyzed C7‐Formylmethylation or Sequential Acetalization of Indolines with Vinylene Carbonate in Different Solvents DOI
Min Liu, Kelu Yan, Jiangwei Wen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(9), С. 1580 - 1586

Опубликована: Апрель 1, 2022

Abstract The ruthenium‐catalyzed C7‐formylmethylation or sequential acetalization of indolines with vinylene carbonate has been realized under simple and easy‐to‐operate reaction systems. Several preliminary mechanistic studies derivatization reactions for the conversion formylmethyl group were also performed. This transformation offers an alternative approach direct C( sp 2 )−H to corresponding acetal structure. magnified image

Язык: Английский

Процитировано

25

Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5717 - 5734

Опубликована: Янв. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Язык: Английский

Процитировано

16

Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate DOI

Jia‐Lin Song,

Lin Xiao,

Shaoyong Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1457 - 1464

Опубликована: Апрель 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Язык: Английский

Процитировано

14

Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis DOI Creative Commons
Killian Onida,

Mohamad Fayad,

Sébastien Norsic

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(11), С. 4282 - 4291

Опубликована: Янв. 1, 2023

The chemical upcycling of poly(bisphenol A carbonate) was carried out through organocatalysis using α-hydroxyketones as nucleophiles, leading to valuable vinylene carbonates.

Язык: Английский

Процитировано

12

Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate DOI
Jiang Nan, Qiong Huang,

Xinran Men

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(26), С. 3571 - 3574

Опубликована: Янв. 1, 2024

Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments

Язык: Английский

Процитировано

5

Rh(III)-Catalyzed C–H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles DOI

Chaoshui Liu,

Qiuzi Dai,

Yaqian Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7281 - 7289

Опубликована: Май 19, 2023

A novel protocol for synthesizing N-alkyl indoles from readily available N-nitrosoanilines and iodonium ylides through the rhodium(III)-catalyzed C-H bond activation/intramolecular cyclization reaction has been described. This strategy employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, proceeds with moderate yields under mild conditions, providing straightforward approach to access structurally diverse valuable indole derivatives.

Язык: Английский

Процитировано

11

Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions DOI Open Access

Xiaofan Cui,

Rémi Chauvin, Chao Pi

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3400 - 3412

Опубликована: Сен. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Язык: Английский

Процитировано

11

Carboxylic Acid-Enabled Vinylene Transfer Reaction by Co(III) Catalyst: Scope and Applications to the Five-Step Total Synthesis of Protoberberine Alkaloids Containing Free Hydroxyl Group without Protection DOI
Ying Song, Ruimin Li,

Jintong Bai

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3238 - 3250

Опубликована: Фев. 14, 2024

A Co(III)-catalyzed vinylene transfer reaction enabled by carboxylic acid is presented. This redox-neutral transformation tolerates various functional groups, including free hydroxyl and features practicality. Five-step routes based on the Heck annulation have been devised to total synthesis of 8-oxodehydrodiscretamine 2-demethyl-oxypalmatine without protection functionality.

Язык: Английский

Процитировано

3

Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent DOI
Jiang Nan, Hanqing Zhang, Lanxin Zhu

и другие.

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

Опубликована: Апрель 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Язык: Английский

Процитировано

0

Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol DOI
Vikash Kumar, Parthasarathy Gandeepan

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(44)

Опубликована: Сен. 27, 2023

Abstract A mild and convenient synthesis of 3,4‐unsubstituted isoquinolones has been achieved from N ‐methoxybenzamides vinylene carbonate as an acetylene surrogate with a versatile rhodium(III) catalyst. The reaction proceeded at room temperature in biomass derived ethanol solvent. This protocol avoids the use stoichiometric external oxidant, served internal oxidant. C−H/N−H activation annulation manifold broad substrate scope excellent levels regioselectivities. preliminary mechanistic studies suggest facile reversible chelation‐assisted C−H rhodation. Diversification provide access to 4‐substituted isoquinolines, which are complementary previously reported protocols.

Язык: Английский

Процитировано

8