Boric Acid Catalyzed Direct Amidation between Amino-Azaarenes and Carboxylic Acids

被引：13

作者：

Yun, Fan ^{[1
]}

Cheng, Chunhui ^{[1
]}

Zhang, Jing ^{[1
]}

Li, Jingxuan ^{[1
]}

Liu, Xia ^{[1
]}

Xie, Rui ^{[1
]}

Tang, Pingwah ^{[1
]}

Yuan, Qipeng ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Organ & Med Chem Div, Coll Life Sci & Technol, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 07期

基金：

美国国家科学基金会;

关键词：

amidation; boric acid; azaarenes; aminopyridine; N; N'; N'-tetramethylpropane-1; 3-diamine; AMIDE BOND FORMATION; ORGANOBORON COMPOUNDS; COUPLING REAGENTS; ORGANIC-SYNTHESIS; DERIVATIVES; INHIBITORS;

D O I：

10.1055/s-0036-1588126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and facile boric acid catalyzed direct amidation between amino-azaarene compounds and carboxylic acids has been developed. The amidation proceeded cleanly and provided good to excellent yields of the desired amides. Boric acid is a green and inexpensive catalyst. We have also found that N,N,N',N'-tetramethylpropane-1,3-diamine acted as an additive accelerating this boric acid catalyzed amidation. A mixed acid anhydride is postulated to be the active intermediate responsible for this successful amidation. This direct amidation is an atom- and step-economical reaction.

引用

页码：1583 / 1596

页数：14

共 50 条

[1] TiF4-catalyzed direct amidation of carboxylic acids and amino acids with amines
Alawaed, Abdulkhaliq A.
Ramachandran, P. Veeraraghavan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (09) : 1915 - 1919
[2] TiF4-catalyzed direct amidation of carboxylic acids and amino acids with amines
Alawaed, Abdulkhaliq A.
Ramachandran, P. Veeraraghavan
Organic and Biomolecular Chemistry, 2024, 22 (09): : 1915 - 1919
[3] Boric acid-grafted biochar (BoAB) for the direct amidation of carboxylic acids and amines
Singh, Adhish
Kapoor, Mohit
NEW JOURNAL OF CHEMISTRY, 2024, 48 (19) : 8589 - 8596
[4] 3-Quinoline Boric Acid as an Efficient Catalyst for the Direct Amidation of Carboxylic Acids at Room Temperature
Dingmin, Huang
Haotian, Sun
Zhenwei, Wang
Hao, Liu
Xianbin, Su
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2023, 44 (06):
[5] Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines
Wang, Chen
Yu, Hai-Zhu
Fu, Yao
Guo, Qing-Xiang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (13) : 2140 - 2146
[6] Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis
Liu, Shouxin
Yang, Yihua
Liu, Xinwei
Ferdousi, Farhana K.
Batsanov, Andrei S.
Whiting, Andrew
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) : 5692 - 5700
[7] Direct Amidation of Carboxylic Acids with Nitroarenes
Wang, Shao-Peng
Cheung, Chi Wai
Ma, Jun-An
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 13922 - 13934
[8] Boric Acid-Catalyzed Direct Condensation of Carboxylic Acids with Benzene-1,2-diamine into Benzimidazoles
Maras, Nenad
Kocevar, Marijan
HELVETICA CHIMICA ACTA, 2011, 94 (10) : 1860 - 1874
[9] Ru-catalyzed direct amidation of carboxylic acids with N-substituted formamides
Bi, Xiaojing
Li, Junchen
Shi, Enxue
Wang, Hongmei
Gao, Runli
Xiao, Junhua
TETRAHEDRON, 2016, 72 (50) : 8210 - 8214
[10] Direct Boronic Acid Promoted Amidation of Carboxylic Acids with Poorly Nucleophilic Amines
Zhou, Jingning
Paladino, Marco
Hall, Dennis G.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (41)

← 1 2 3 4 5 →