Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions

被引：4

作者：

Zeng, Yao-Fu ^{[1
,2
]}

Li, Yi-Na ^{[1
]}

Zhang, Na-Na ^{[2
]}

Kang, Huan ^{[2
]}

Duan, Pan ^{[2
]}

Xiao, Fang ^{[1
]}

Guo, Yu ^{[1
,2
]}

Wen, Xianghao ^{[3
]}

机构：

[1] Univ South China, Inst Pharm & Pharmacol, Hengyang 421001, Peoples R China

[2] Univ South China, Sch Pharmaceut Sci, Hengyang 421001, Peoples R China

[3] Univ South China, Affiliated Nanhua Hosp, Hengyang 421001, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 19期

关键词：

aryl amines; amidation; acetonitrile; diazotization; acetamides; coupling reaction; NITRILES; AMIDATION; ACYLATION; EFFICIENT; AMIDES; SALTS;

D O I：

10.1055/s-0039-1690237

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

引用

页码：2169 / 2172

页数：4

共 50 条

[1] A Metal-Free Synthesis of N-Aryl Carbamates under Ambient Conditions
Guo, Wusheng
Gonzalez-Fabra, Joan
Bandeira, Nuno A. G.
Bo, Carles
Kleij, Arjan W.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (40) : 11686 - 11690
[2] Electrochemical Synthesis of Aryl Sulfonates from Sodium Sulfinates and Phenols under Metal-Free Conditions
Fu Zhengjiang
Yang Zhenjiang
Sun Li
Yin Jian
Yi Xuezheng
Cai Hu
Lei Aiwen
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (02) : 600 - 606
[3] Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions
Reddy, Nagireddy Veera
Kumar, Pailla Santhosh
Reddy, Peddi Sudhir
Kantam, Mannepalli Lakshmi
Reddy, Kallu Rajender
NEW JOURNAL OF CHEMISTRY, 2015, 39 (02) : 805 - 809
[4] Synthesis of N-arylacetamides via amination of aryltriazenes with acetonitrile under metal-free and mild conditions
Wang, Bin
Cao, Dawei
Ma, Xuecheng
Feng, Yun
Zhang, Lin
Zhang, Yonghong
Liu, Chenjiang
ARABIAN JOURNAL OF CHEMISTRY, 2021, 14 (06)
[5] Synthesis of Aryl Sulfides by Metal-Free Arylation of Thiols with Diaryliodonium Salts under Basic Conditions
Sarkar, Sudeep
Wojciechowska, Natalia
Rajkiewicz, Adam A.
Kalek, Marcin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (02)
[6] Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions
Xiong, Biquan
Wang, Gang
Xiong, Tao
Wan, Liming
Zhou, Congshan
Liu, Yu
Zhang, Panliang
Yang, Changan
Tang, Kewen
TETRAHEDRON LETTERS, 2018, 59 (32) : 3139 - 3142
[7] Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions
Purkait, Nibadita
Kervefors, Gabriella
Linde, Erika
Olofsson, Berit
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (35) : 11427 - 11431
[8] A Green Procedure for the Diazotization-Iodination of Aromatic Amines under Aqueous, Strong-Acid-Free Conditions
Trusova, Marina E.
Krasnokutskaya, Elena A.
Postnikov, Pavel S.
Choi, Younghwa
Chi, Ki-Whan
Filimonov, Victor D.
SYNTHESIS-STUTTGART, 2011, (13): : 2154 - 2158
[9] Base-Controlled Three Component Reactions of Amines, Elemental Sulfur, and Styrenes: Synthesis of Thioamides under Metal-Free Conditions
Zhang, Pingshun
Chen, Wanzhi
Liu, Miaochang
Wu, Huayue
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23) : 14269 - 14276
[10] An Umpolung Route to Amides from α-Aminonitriles under Metal-Free Conditions
Swetha, Sathyendran
Senadi, Gopal Chandru
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) : 2872 - 2882

← 1 2 3 4 5 →