1,4-carbonylative addition of arylboronic acids to methyl vinyl ketone: a new synthetic tool for rapid furan and pyrrole synthesis

被引:25
作者
Chochois, Helene [1 ]
Sauthier, Mathieu [1 ]
Maerten, Eddy [1 ]
Castanet, Yves [1 ]
Mortreux, Andr [1 ]
机构
[1] ENSCL, USTL, UMR 8181, CNRS,Unite Catalyse & Chim Solide, F-59652 Villeneuve Dascq, France
关键词
D O I
10.1016/j.tet.2006.09.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rhodium catalysed 1,4-carbonylative addition of arylboronic acids to methyl vinyl ketone under carbon monoxide pressure was studied. High yields of 1,4-diketones were obtained using a catalytic system formed from Rh(COD)(2)BF4 (COD= 1,5-cyclooctadiene) and triphenylphosphine even at very low catalyst loading (0.02 mol %). A short synthetic procedure combining this carbonylation reaction with a subsequent cyclisation step affords pyrroles or furans. (c) 2006 Elsevier Ltd. All rights, reserved.
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页码:11740 / 11746
页数:7
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