Synthesis of C9,C10-Diheteroarylated Phenanthrenes via Palladium-Catalyzed C-H Bond Activation

被引：2
作者：
Bouzayani, Bilel [1 ,2 ]
Ben Salem, Ridha [2 ]
Soule, Jean-Francois [1 ]
Doucet, Henri [1 ]
机构：
[1] Univ Rennes, CNRS, UMR 6226, ISCR, F-35000 Rennes, France
[2] Univ Sfax, Fac Sci Sfax, Lab Chim Organ LR 17ES08, Route Soukra Km 4, Sfax 3038, Tunisia
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 44期
关键词：
Palladium; Homogeneous catalysis; C-H activation; Coupling; Phenanthrenes; Heteroarenes; DIRECT ARYLATION; COUPLING REACTION; AZOLES; REGIOSELECTIVITY; HETEROAROMATICS; HETEROARENES; HETEROATOM; THIOPHENE; ACCESS;
D O I：
10.1002/ejoc.201800533
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactivity of positions C9 and C10 of 9- or 10-bromophenanthrenes in palladium-catalyzed direct heteroarylations was investigated. A wide variety of heteroarenes such as thiazoles, (benzo)thiophenes, (benzo)furans, pyrroles, selenophenes or imidazopyridazines was successfully introduced at phenanthrene C9-position via palladium-catalyzed direct arylations, using 0.5-0.1 mol-% of phosphine-free Pd(OAc)(2) catalyst. Then, C10-bromination of the 9-heteroarylated phenanthrenes, followed by a second palladium-catalyzed direct heteroarylation gives access to symmetrical and non-symmetrical 9,10-di(heteroaryl)phenanthrenes.
引用
收藏
页码：6092 / 6100
页数：9
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