Copper-(II) Catalyzed N-Formylation and N-Acylation of Aromatic, Aliphatic, and Heterocyclic Amines and a Preventive Study in the C-N Cross Coupling of Amines with Aryl Halides

被引:41
作者
Sonawane, Rahul B. [1 ]
Rasal, Nishant K. [1 ]
Bhange, Dattatraya S. [1 ]
Jagtap, Sangeeta V. [1 ]
机构
[1] Savitribai Phule Pune Univ, Baburaoji Gholap Coll, Dept Chem, Pune 411027, Sangvi, India
关键词
1,2, 4-triazole; C-N cross coupling reaction; Cu-(II) catalyzed; N-acylation; N-formylation; SOLVENT-FREE CONDITIONS; HIGHLY EFFICIENT PROCEDURE; ROOM-TEMPERATURE; CARBON-DIOXIDE; ULTRASOUND-IRRADIATION; RECYCLABLE CATALYST; AEROBIC OXIDATION; AMMONIUM FORMATE; SECONDARY-AMINES; SULFURIC-ACID;
D O I
10.1002/cctc.201800609
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A Cu-(II) catalyzed N-formylation and N-acylation of amines with moderate to excellent yields, using N, N-dimethyl formamide (DMF) and N, N-dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4-triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N-formylation and N-acylation impurities in the C-N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.
引用
收藏
页码:3907 / 3913
页数:7
相关论文
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[41]   Copper(II)-Catalyzed Oxidative Coupling of Anilines, Methyl Arenes, and TMSN3 via C(sp3/sp2)-H Functionalization and C-N Bond Formation [J].
Mahesh, Devulapally ;
Satheesh, Vanaparthi ;
Kumar, Sundaravel Vivek ;
Punniyamurthy, Tharmalingam .
ORGANIC LETTERS, 2017, 19 (24) :6554-6557