An efficient route to 2,6-disubstituted styrenes via the palladium-catalyzed [4+2] cyclodimerization of conjugated enynes

被引：41
|
作者：
Gevorgyan, V [1 ]
Tando, K [1 ]
Uchiyama, N [1 ]
Yamamoto, Y [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 20期
关键词：
D O I：
10.1021/jo980967+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and general method for the synthesis of 2,6-disubstituted styrenes 5 via the palladium-catalyzed [4+2] homobenzannulation of conjugated enynes 4 was developed. In all cases, the reactions proceeded in regiospecific manner, affording the disubstituted styrenes, bearing various functional groups at the 2 and 6 positions of the benzene ring, as a single reaction product in good to excellent yields. Initial attempts at cross-cycloaddition of two different enynes indicated low degrees of chemoselectivity of this process. Accordingly, the cross-dimerization products 6 in all cases were accompanied with notable amounts of the chemoisomeric homodimers 5.
引用
收藏
页码：7022 / 7025
页数：4
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