Copper-Catalyzed Coupling of N-Tosylhydrazones with Amines: Synthesis of Fluorene Derivatives

被引:44
作者
Aziz, Jessy [1 ]
Frison, Gilles [2 ,3 ]
Gomez, Montserrat [4 ,5 ]
Brion, Jean-Daniel [1 ]
Hamze, Abdallah [1 ]
Alami, Mouad [1 ]
机构
[1] Univ Paris 11, Equipe Labellisee Ligue Canc, Lab Chim Therapeut, CNRS,BioCIS UMR 8076,LabEx LERMIT,Fac Pharm, F-92296 Chatenay Malabry, France
[2] Ecole Polytech, Dept Chem, Lab Chim Mol, F-91128 Palaiseau, France
[3] CNRS, F-91128 Palaiseau, France
[4] Univ Toulouse 3, UPS, Lab Heterochim Fondamentale & Appl, F-31062 Toulouse 9, France
[5] CNRS UMR 5069, F-31062 Toulouse 9, France
关键词
N-tosylhydrazones; C-N/C-C bond formation; autotandem catalysis; carbenoid; fluoren-9H-amines; DIAZO-COMPOUNDS; MIGRATORY INSERTION; BOND FORMATION; METAL CARBENE; PALLADIUM; CYCLIZATION; HYDRAZONES; REAGENTS;
D O I
10.1021/cs5014877
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
An original formation of one C-N bond and one C-C bond on the same carbenic center has been developed. This approach involves a copper-catalyzed cross-coupling reaction between 2'-bromo-biaryl-N-tosylhydrazones and different amines leading to 9H-fluoren-9-amine derivatives. This reaction proceeds under mild conditions in glycerol, an inexpensive and environmentally friendly solvent, without adding any external ligand.
引用
收藏
页码:4498 / 4503
页数:6
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