☆ 4.8 Article

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I2-Aqueous NH3

ORGANIC LETTERS (2016)

期刊

ORGANIC LETTERS

卷 18, 期 4, 页码 784-787

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b00048

关键词

-

类别

Chemistry, Organic

资金

Ministry of Education, Culture, Sports, Science, and Technology, Japan [25105710]
Grants-in-Aid for Scientific Research [15K17819, 15K05418] Funding Source: KAKEN

向作者/读者索取更多资源

Protocol

Reagent

摘要

A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2'-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, followed by reaction with molecular iodine and aq NH3 in one pot. It was found that aryl a-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

Copper-Catalyzed Direct sp2 C-H Silylation of Arylamides Using Disilanes

Writhabrata Sarkar, Aniket Mishra, Arup Bhowmik, Indubhusan Deb

Summary: A copper-catalyzed method has been developed for the direct intermolecular ortho-silylation of benzamides, providing organosilane products in moderate to high yields. This method is operationally simple, tolerates a wide range of functional groups, and has been demonstrated to be practical and effective on a gram-scale experiment for constructing C-Si bonds in synthetic organic chemistry.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct alkylation of N,N-dialkyl benzamides with methyl sulfides under transition metal-free conditions

Can-Can Bao, Hui-Zhen Du, Yan-Long Luo, Bing-Tao Guan

Summary: A method of direct alkylation of benzamides with methyl sulfides promoted by the base LDA has been reported, successfully achieving an efficient and selective synthesis of alpha-sulfenylated ketones.

COMMUNICATIONS CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Zinc-Catalyzed Chemoselective Reduction of Nitriles to N-Silylimines through Hydrosilylation: Insights into the Reaction Mechanism

Rajata Kumar Sahoo, Sharanappa Nembenna

Summary: A highly chemoselective mono-hydrosilylation method for nitriles using a N,N'-PRIME-chelated conjugated bis-guanidinate supported zinc hydride catalyst (Zn-1) is reported. Compared to a similar pre-catalyst (Zn-2), Zn-1 exhibits higher efficiency and selectivity in reducing nitriles to N-silylimines. Mechanistic studies reveal the formation of zinc vinylidenamido complexes (Zn-1 & PRIME; and Zn-2 & PRIME;) via the insertion of the CN bond of nitriles into Zn-H.

INORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Multidisciplinary Sciences

Direct transformation of n-alkane into all-trans conjugated polyene via cascade dehydrogenation

Xuechao Li, Kaifeng Niu, Junjie Zhang, Xiaojuan Yu, Haiming Zhang, Yuemin Wang, Qing Guo, Pengdong Wang, Fangsen Li, Zhengming Hao, Chaojie Xu, Yanning Tang, Zhichao Xu, Shuai Lu, Peng Liu, Guigu Xue, Yen Wei, Lifeng Chi

Summary: Selective cascade dehydrogenation of n-alkane molecules under surface constraints can yield monodispersed all-trans conjugated polyenes with unprecedented length controllability, demonstrating potential for diverse functionalities and molecular wiring applications.

NATIONAL SCIENCE REVIEW (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Direct Carbonylation of Bromoacetonitrile to Synthesize 2-Cyano-N-acetamide and 2-Cyanoacetate Compounds

Zhi-Peng Bao, Xiao-Feng Wu

Summary: This article develops an efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of 2-cyano-N-acetamide and 2-cyanoacetate compounds. The reaction proceeds under mild conditions via a radical intermediate, suitable for late-stage functionalization. Gram-scale experiment was successfully performed with low catalyst loading, yielding the target product excellently. Additionally, this transformation can be carried out under atmospheric pressure and provides alternative routes to drug precursors.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

添加到收藏夹

Article Multidisciplinary Sciences

Chemoselective carbene insertion into the N-H bonds of NH3•H2O

Zhaohong Liu, Yong Yang, Qingmin Song, Linxuan Li, Giuseppe Zanoni, Shaopeng Liu, Meng Xiang, Edward A. Anderson, Xihe Bi

Summary: This study reports a chemoselective N-H insertion reaction of inexpensive aqueous ammonia using a TpBr3Ag-catalyzed two-phase system, leading to the conversion into value-added primary amines. The reaction exhibits high chemoselectivity and allows the coupling of inorganic nitrogen sources with diazo compounds or N-triftosylhydrazones to produce useful primary amines.

NATURE COMMUNICATIONS (2022)

添加到收藏夹

Review Biochemistry & Molecular Biology

The Biosynthesis and Metabolism of the N-Acylated Aromatic Amino Acids: N-Acylphenylalanine, N-Acyltyrosine, N-Acyltryptophan, and N-Acylhistidine

Suzeeta Bhandari, Kirpal S. Bisht, David J. Merkler

Summary: Fatty acid amides are lipids composed of a fatty acid and a biogenic amine. This review focuses on a lesser-known sub-class of fatty acid amides called N-acyl aromatic amino acids (NA-ArAAs). The review highlights the identified NA-ArAAs from biological sources and presents information on their biosynthesis, degradation, enzymatic modification, and transport, as well as their cellular functions. The aim of this review is to stimulate future research on this underappreciated sub-class of the fatty acid amide family.

FRONTIERS IN MOLECULAR BIOSCIENCES (2022)

添加到收藏夹

Article Chemistry, Organic

Copper(II)-Catalyzed Direct C-H (Hetero)arylation at the C3 Position of Indoles Assisted by a Removable N,N-Bidentate Auxiliary Moiety

Hai-Feng Xu, You-Lu Pan, Gang-Jian Li, Xu-Yang Hu, Jian-Zhong Chen

Summary: A newly established method for the regioselective arylation of inert C3-H bonds in indoles using effective copper-mediated catalysis with the aid of a removable PIP group is reported. The method shows high compatibility with functional groups between coupling partners, leading to simplicity in operation and yielding desired arylated products in good to excellent yields up to 97%. Additionally, the PIP-derived amide moiety can be easily removed under mild reaction conditions to produce useful indole carboxylic acids for further transformation.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Physical

Selective direct conversion of aqueous ethanol into butadiene via rational design of multifunctional catalysts

Kangzhou Wang, Xiaobo Peng, Chengwei Wang, Weizhe Gao, Na Liu, Xiaoyu Guo, Yingluo He, Guohui Yang, Lilong Jiang, Noritatsu Tsubaki

Summary: Researchers reported a highly efficient multifunctional Y-ZnZr/Si-beta catalyst for direct AETB conversion, showing outstanding ethanol conversion and butadiene selectivity. Furthermore, the catalyst exhibited excellent regeneration ability.

CATALYSIS SCIENCE & TECHNOLOGY (2022)

添加到收藏夹

Article Chemistry, Physical

DMAPO/Boc2O-Mediated One-Pot Direct N-Acylation of Less Nucleophilic N-Heterocycles with Carboxylic Acids

Atsushi Umehara, Soma Shimizu, Makoto Sasaki

Summary: This report presents a practical and operationally simple method for the direct N-acylation of less nucleophilic heterocycles and amides with carboxylic acids. The method utilizes the DMAPO/Boc(2)O system and does not require pre-activation of substrates. It demonstrates high yield, excellent functional group tolerance, and broad substrate scope, making it suitable for both academic and industrial laboratories.

CHEMCATCHEM (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of N-aryl-substituted azacycles

Ying Lin, Dongyang Li, Jingjing Zhang, Zhi Tang, Long Liu, Tianzeng Huang, Chunya Li, Tieqiao Chen

Summary: The protocol efficiently synthesizes N-aryl-substituted azacycles using aryl amines and cyclic ethers with I-2/NaH2PO2, yielding products with good functional group tolerance. The reaction can be easily scaled up to produce gram-scale amounts and further chemical modifications of the products enable useful transformations of the quinoline ring, including bromination and acetylation.

NEW JOURNAL OF CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

(ItOctyl) - pushing the limits of : highly hindered electron-rich N-aliphatic N-heterocyclic carbenes

Md. Mahbubur Rahman, Guangrong Meng, Elwira Bisz, Blazej Dziuk, Roger Lalancette, Roman Szostak, Michal Szostak

Summary: ItBu is the most important and versatile N-alkyl N-heterocyclic carbene in organic synthesis and catalysis. In this study, we report the synthesis, characterization, and catalytic activity of ItOct (ItOctyl), higher homologues of ItBu. ItOct and SItOct, a new ligand class, have been commercialized to facilitate access for researchers in organic and inorganic synthesis. We demonstrate that the replacement of t-Bu side chain with t-Oct results in the highest steric volume of N-alkyl N-heterocyclic carbenes reported to date, while retaining important electronic properties. Coordination chemistry to various metals and beneficial effects on catalysis are also described.

CHEMICAL SCIENCE (2023)

添加到收藏夹

Article Chemistry, Applied

Synthesis of Bulky N-Acyl Heterocycles by DMAPO/Boc2O-Mediated One-Pot Direct N-Acylation of Less Nucleophilic N-Heterocycles with a-Fully Substituted Carboxylic Acids

Atsushi Umehara, Soma Shimizu, Makoto Sasaki

Summary: This report presents a general method for the direct N-acylation of N-heterocycles using the DMAPO/Boc(2)O system. This one-pot method allows for the synthesis of bulky N-acyl heterocycles from less nucleophilic N-heterocycles and sterically hindered carboxylic acids. The protocol has also been successfully applied to the one-pot N-acylation of 7-azaindoles.

ADVANCED SYNTHESIS & CATALYSIS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

The Facile Hydrolysis of Imidazolinium Chlorides (N-Heterocyclic Carbene Precursors) Under Basic Aqueous Conditions

Nedra Touj, Jerwin Jay Taping, Nikolay Tumanov, Johan Wouters, Lionel Delaude

Summary: The hydrolysis of imidazolinium chlorides occurs readily in a basic water/dichloromethane biphasic mixture at room temperature. Substrates with alkyl or aryl substituents on their nitrogen atoms led to high yields of gamma-aminoformamides. Bulky alkyl or aryl groups on the formamide moiety resulted in high stereoisomeric purity of the (E)-isomer. The presence of bulky aromatic substituents on the nitrogen atoms slowed down the hydrolysis of certain imidazolinium chlorides. The counteranion was found to have a critical influence on the reactivity of imidazolinium cations.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Overlooked potential of N,N-bidentate directing-groups in Ni-catalyzed C-H functionalization of benzamides

Weirong Wu, Xufang Zhao, Guang Chen, Lingjun Liu, Yulin Li, Tao Chen, Tony D. James, Yuxia Liu

Summary: The Ni-catalyzed reactions of benzamides with bicyclic alkenes were investigated using DFT calculations. A novel N-H deprotonation circumventing catalytic mechanism was proposed, and the overlooked aspects of functionalized N,N-bidentate directing groups were pointed out to be useful for designing new catalytic reactions.

CHEMICAL COMMUNICATIONS (2023)

添加到收藏夹

暂无数据

暂无数据

© Peeref 2019-2024. All rights reserved.