REMARKABLE REVERSAL OF THE REGIOSELECTIVITY IN THE PALLADIUM-CATALYZED HYDROCARBONATION REACTION OF ALLENES WITH METHYLMALONONITRILE

被引:61
作者
YAMAMOTO, Y
ALMASUM, M
FUJIWARA, N
ASAO, N
机构
[1] Department of Chemistry, Faculty of Sciences, Tohoku University, Sendai
关键词
D O I
10.1016/0040-4039(95)00403-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium catalyzed addition of methylmalononitrile 4a to arylallenes 3 affords the internal adducts 5 and 6 either predominantly or exclusively when an electron-withdrawing group is present at the para-position, whereas it gives the terminal adduct 7 exclusively when an electron-donating group is present at the para-position.
引用
收藏
页码:2811 / 2814
页数:4
相关论文
共 13 条
[1]  
Yamamoto, Al-Masum, Asao, J. Am. Chem. Soc., 116, (1994)
[2]  
Cazes, Pure & Appl. Chem., 62, (1990)
[3]  
Gauthier, Cazes, Gore, Tetrahedron Lett., 32, (1991)
[4]  
Chaptal, Gotleland, Grandjean, Cazes, Gore, Tetrahedron Lett., 32, (1991)
[5]  
Besson, Bazin, Gore, Cazes, Tetrahedron Lett., 35, (1994)
[6]  
Shimizu, Tsuji, Palladium-catalyzed synthesis of 2,3-disubstituted allylamines by regioselective aminophenylation or aminoalkenylation of 1,2-dienes., Chemistry Letters, (1984)
[7]  
Shimizu, Sugiura, Tsuji, J. Org. Chem., 50, (1985)
[8]  
Larock, Varaprath, Lau, Fellows, J. Am. Chem. Soc., 106, (1984)
[9]  
Larock, Berrios-Pena, Fried, J. Org. Chem., 56, (1991)
[10]  
Ma, Negishi, J. Org. Chem., 59, (1994)