New method of alkenylation of anilines by acetylene compounds in the superacid HSO₃F

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• 作者：Andrey O. Shchukin ; Aleks ; er V. Vasilyev ; Andrey P. Rudenko
• 关键词：Arene alkenylation ; Friedel– ; Crafts reactions ; Acetylene compounds ; Anilines ; Superacids ; Fluorosulfonic acid
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：30 June 2008
• 年：2008
• 卷：64
• 期：27
• 页码：6334-6340
• 全文大小：702 K

文摘

Vinyl cations, generated by protonation of the triple bond of ,β-alkynylcarbonyl compounds in the superacid HSO₃F, react efficiently with arylammonium (anilinium) ions at low temperatures −75 and −30 °C in 30–75 min with the formation of Friedel–Crafts-type products of anilinium ring alkenylation in 14–62 % yields. Regio- and stereoselectivity of such electrophilic aromatic substitution has been studied in detail.