A SYNTHESIS OF HIGHLY SUBSTITUTED AROMATICS THROUGH REGIOCONTROLLED CONSTRUCTION OF CYCLOBUTENONES BEARING UNSATURATED SUBSTITUENTS AT THE 4-POSITION

被引:74
作者
KRYSAN, DJ [1 ]
GURSKI, A [1 ]
LIEBESKIND, LS [1 ]
机构
[1] EMORY UNIV,DEPT CHEM,ATLANTA,GA 30322
关键词
D O I
10.1021/ja00030a043
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2,3-Substituted 4-chloro-2-cyclobutenones, prepared by regiospecific transformations of substituted cyclobutenediones, undergo palladium-catalyzed cross-coupling with vinyl- and arylstannanes and vinylzirconium reagents to form 4-R(unsat)-2-cyclobutenones. On thermolysis (100-degrees-C), these substrates transform into substituted phenols in high yield. A pentasubstituted aromatic and a variety of tri- and tetrasubstituted aromatic compounds were prepared in a regiospecific fashion using this chemistry.
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页码:1412 / 1418
页数:7
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