Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds DOI
Xiaogang Wang, Chi Yang, Di Chen

и другие.

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

Опубликована: Ноя. 28, 2024

A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly densely functionalized indoles. This new catalytic process represents first example a cascade intramolecular nucleophilic cyclization by N-H insertion amines. Various could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to heterocyclic analogues not easily accessible other methods.

Язык: Английский

Oxygen Migration–Defluorination Strategy Enables the Aminocarbonylation of Enaminones with o-Aminobenzamides and CF2Br2 DOI

Wanqing Zuo,

Renhua Zheng,

Yinghong Huang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 24, 2025

The development of different concept approaches and user-friendly carbonyl surrogates for aminocarbonylation is highly desirable. Herein, we report the photocatalytic enaminones with easily available o-aminobenzamides CF2Br2 through an oxygen migration-defluorination strategy. reaction features switchable transformation construction carbamoyl-substituted enol products allows expedient synthesis fully substituted maleimides under mild conditions.

Язык: Английский

Процитировано

2
Substituent-Controlled Regiodivergent Rearrangement of Gramine Ammonium Ylide DOI
Yu Shen,

Ao Huang,

Xiyao Lu

и другие.

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

Опубликована: Янв. 30, 2025

The complicated mechanism makes the regiodivergent rearrangement of ammonium ylide seem to be out reach. Herein, we reported a gramine well controlled by substituents. Density functional theory studies reveal that with more steric hindrance substituent 2-diazo-2-arylacetate goes through stepwise yield both kinetically and thermodynamically preferred [1,2]-rearrangement product. In contrast, less ethyl diazoacetate concerted generate [2,3]-rearrangement product, which is favored as result release ring strain in transition state. This study would open up avenues grasp ylide, will promote application skeletal editing synthesis complex natural products.

Язык: Английский

Процитировано

1
Assembly of Diverse Allenes via Activator-Free Palladium-Catalyzed Regioselective γ-Arylation of Propargylamines with Boronic Acids DOI
Yan Sun,

Ya Pan,

Tao Zhao

и другие.

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

Опубликована: Фев. 7, 2025

Controlling the reaction selectivity to achieve a precision synthesis is constant concern for chemists. Here, we report palladium-catalyzed deaminative coupling of propargylamines with arylboronic acids generate allene skeletons. Importantly, this approach allows regioselective γ-arylation unactivated propargyl tertiary amines access various allenes in absence amino-activating reagents. We present wide range and boronic demonstrate synthetic application target products construct valuable compounds.

Язык: Английский

Процитировано

0
Difluorocarbene-Mediated Trimethylsilylation of Nucleophiles with HCF2N(TMS)2 as a Silylation Reagent DOI

Hao Ruan,

Dong Zhu,

Jingwei Zhao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

Described herein is the trimethylsilylation of various nucleophiles using a combination HCF3 and NaHMDS. This facile protocol enables rapid construction alkynylsilanes, silyl enol ethers, etc., under mild conditions. Detailed mechanistic studies indicate that trimethylsilicon intermediate formed in situ can be readily attacked by nucleophiles, with activation base NaHMDS difluorocarbene. work first utilizes structure HMDS as silicon source terminal alkynes.

Язык: Английский

Процитировано

0
Difluorocarbene-Enabled Dehydration of Primary Amides To Access Nitriles DOI

Bofan Feng,

Huosheng Guo,

Xiaosha Wang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 16, 2025

A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.

Язык: Английский

Процитировано

0
Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds DOI
Xiaogang Wang, Chi Yang, Di Chen

и другие.

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

Опубликована: Ноя. 28, 2024

A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly densely functionalized indoles. This new catalytic process represents first example a cascade intramolecular nucleophilic cyclization by N-H insertion amines. Various could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to heterocyclic analogues not easily accessible other methods.

Язык: Английский

Процитировано

0