Triorganoindium Reagents in Selective Palladium-Catalyzed CrossCoupling with lodoimidazoles: Synthesis of Neurodazine

被引:20
作者
Perez-Caaveiro, Cristina
Perez Sestelo, Jose
Montserrat Martinez, M. [1 ]
Sarandeses, Luis A.
机构
[1] Univ A Coruna, Dept Quim Fundamental, E-15071 La Coruna, Spain
关键词
CROSS-COUPLING REACTIONS; INDIUM ORGANOMETALLICS; BUILDING-BLOCKS; IMIDAZOLE RING; IONIC LIQUID; HETEROCYCLES; POTENT; FUNCTIONALIZATION; 2-IMIDAZOLES; DERIVATIVES;
D O I
10.1021/jo501664p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triorganoindium reagents (R3In, R = aryl, heteroaryl, alkynyl) react selectively under palladium catalysis with N-benzyl-2,4,5-triiodoimidazole to afford the C-2 monocoupling products. The reaction proceeds efficiently for a variety of aryl- and heteroarylindium reagents with the transfer of all three organic groups attached to the metal. The coupling products can be used in a subsequent two-fold cross-coupling to give trisubstituted imidazoles in good yields. This approach was employed to synthesize neurodazine and analogues in good yields. (Chemical Equation Presented). © 2014 American Chemical Society.
引用
收藏
页码:9586 / 9593
页数:8
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