Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides.: Synthesis of C-aryl glycals

被引:78
作者
Lehmann, U [1 ]
Awasthi, S [1 ]
Minehan, T [1 ]
机构
[1] Harvey Mudd Coll, Dept Chem, Claremont, CA 91711 USA
关键词
D O I
10.1021/ol0345428
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl2Pd(PPh3)(2) to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.
引用
收藏
页码:2405 / 2408
页数:4
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