Remote Aryl Cyanation via Isocyanide鈥揅yanide Rearrangement on Tosylmethyl Isocyanide Derivatives

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• 作者：Anna Coppola ; Patricia S谩nchez-Alonso ; David Sucunza ; Carolina Burgos ; Ram贸n Alajar铆n ; Julio Alvarez-Builla ; Marta E. G. Mosquera ; Juan J. Vaquero
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：July 5, 2013
• 年：2013
• 卷：15
• 期：13
• 页码：3388-3391
• 全文大小：253K
• 年卷期：v.15,no.13(July 5, 2013)
• ISSN：1523-7052

文摘

The reaction of alkyl tosylmethyl isocyanides and 2-bromobenzyl bromides in the presence of t-BuLi gives rise to a cascade reaction to give unexpected 2-substituted 2,3-dihydro-1H-indenimines which, upon treatment with t-BuOK, rearrange to 2-vinylbenzonitriles in high overall yields. This simple procedure represents a new approach to the synthesis of aromatic nitriles via isocyanide鈥揷yanide interconversion.