An efficient bismuth(III) chloride-catalyzed synthesis of 1,1-diarylalkenes via Friedel-Crafts reaction of acyl chloride or vinyl chloride with arenes

被引：17
|
作者：
Sun, Hongbin
Hua, Ruimao [1 ]
Chen, Songjie
Yin, Yingwu
机构：
[1] Tsinghua Univ, Dept Chem, Key Lab Organ Optoelect & Mol Engn, Minist Educ, Beijing 100084, Peoples R China
[2] Minist Educ, Key Lab Bioorgan Phosphorus Chem, Beijing 100084, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 14期
关键词：
acyl chlorides; arenes; bismuth(III) chloride; 1,1-diarylalkenes; Friedel-Crafts reaction; vinyl chlorides; REVERSE-TRANSCRIPTASE INHIBITORS; ONE-POT SYNTHESIS; ORGANIC-SYNTHESIS; BI(OTF)(3)-CATALYZED ALLYLATION; BUTYL HYDROPEROXIDE; PALLADIUM CATALYSTS; CONJUGATE ADDITION; HOMOALLYL ETHERS; FACILE SYNTHESIS; AROMATIC-AMINES;
D O I：
10.1002/adsc.200606157
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
In the presence of catalytic amount of bismuth(III) chloride, the reactions of acyl chlorides or vinyl chlorides with arenes afforded 1,1-diarylatkenes in 25-82% isolated yield. In the case of the reaction of acyl chlorides with arenes, the procedure includes an initial Friedel-Crafts acylation, subsequent formation of vinyl chlorides and final Friedel-Crafts-type vinylation of another arene molecule with vinyl chloride. This paper reports the first Lewis acid-catalyzed cleavage of the C-Cl bond of vinyl chloride and its application in the synthesis of multiply subtituted alkenes.
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页码：1919 / 1925
页数：7
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