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
共 41 条
[31]   Copper promoted desulfurization and C-N cross coupling reactions: Simple approach to the synthesis of substituted 2-aminobenzoxazoles and 2,5-disubstituted tetrazole amines [J].
Boddapati, S. N. Murthy ;
Saketi, Jagan Mohana Rao ;
Mutchu, Baby Ramana ;
Bollikolla, Hari Babu ;
Adil, Syed Farooq ;
Khan, Mujeeb .
ARABIAN JOURNAL OF CHEMISTRY, 2020, 13 (02) :4477-4494
[32]   C-N cross-coupling organic transformations catalyzed via copper oxide nanoparticles: A review (2016-present) [J].
Arora, Prensha ;
Kumar, Parveen ;
Tomar, Vijesh ;
Sillanpaa, Mika ;
Joshi, Raj Kumar ;
Nemiwal, Meena .
INORGANIC CHEMISTRY COMMUNICATIONS, 2022, 145
[33]   Cu2O-Catalyzed Ullmann-type C-N cross-coupling reaction of carbazole and aryl chlorides [J].
Zhu, Baiyao ;
Xiong, Wenfang ;
Tan, Xiaobin ;
Wu, Wanqing ;
Jiang, Huanfeng .
TETRAHEDRON LETTERS, 2022, 109
[34]   CuF2-Catalyzed C-N Cross-Coupling of Aryl Silanes: Expanding the Scope of Chan-Lam Type Reaction [J].
Talukdar, Vishal ;
Paul, Siddhartha ;
Mondal, Krishanu ;
Das, Parthasarathi .
ADVANCED SYNTHESIS & CATALYSIS, 2025,
[35]   Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C-O, C-N, and C-H Bonds [J].
Cong, Xuefeng ;
Zeng, Xiaoming .
SYNLETT, 2021, 32 (13) :1343-1353
[36]   New efficient ligand for sub-mol % copper-catalyzed C-N cross-coupling reactions running under air [J].
Larsson, Per-Fredrik ;
Astvik, Peter ;
Norrby, Per-Ola .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1909-1915
[37]   Three copper(II) complexes derived from 2-methylquinoline and cyclic secondary amines: Synthesis and catalytic application in C-N bond forming reactions [J].
Jia, Xuefeng ;
He, Jieting .
APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (07)
[38]   Copper- and phosphine-free Sonogashira coupling reactions of aryl iodides catalyzed by an N,N-bis(naphthylideneimino)diethylenetriamine-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions [J].
Bakherad, Mohammad ;
Amin, Amir H. ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Raeissi, Mersad .
TETRAHEDRON LETTERS, 2010, 51 (43) :5653-5656
[39]   Rh-catalyzed C-N coupling ofN-sulfonyl-1,2,3-trizales with secondary amines for regioselective synthesis of phenylvinyl-1,2-diamines [J].
He, Xinwei ;
Wu, Yuhao ;
Zhou, Tongtong ;
Zuo, Youpeng ;
Xie, Mengqing ;
Li, Ruxue ;
Duan, Jiahui ;
Shang, Yongjia .
SYNTHETIC COMMUNICATIONS, 2020, 50 (17) :2685-2697
[40]   Palladium(II)-Catalyzed N-Carbonylative Cross-Coupling Reaction of Sulfoximines with Aryl, Heteroaryl, and Alkenyl Halides Using Tungsten Hexacarbonyl as Carbon Monoxide Source [J].
Han, Sang Hoon ;
Lee, Kyungsup ;
Noh, Hee Chan ;
Lee, Phil Ho .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (09) :2397-2405