Copper cyanide-catalyzed palladium coupling of N-tert-butoxycarbonyl-protected alpha-lithio amines with aryl iodides or vinyl iodides

被引:54
作者
Dieter, RK
Li, SJ
机构
[1] Howard L. Hunter Chem. Laboratory, Clemson University, Clemson
关键词
D O I
10.1021/jo970985b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of (alpha-aminoalkyl)lithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)(2) or [(p-MeOC6H4)(3)P](4)Pd affords 2-aryl substituted amines in modest to good yields. The yields can be improved by use of softer ligands such as AsPh3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupled products are obtained with electron-rich aryl iodides (XArI, X = Me, OMe), and the reaction fails with electron-poor aryl iodides (XArI, X = NO2, CO2Li). Treatment of the (alpha-aminoalkyl)lithium reagents with vinyl iodides and Pd(0)/dppf/CuCN afforded the coupling products in low to modest yields.
引用
收藏
页码:7726 / 7735
页数:10
相关论文
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