Remote Aryl Cyanation via Isocyanide–Cyanide Rearrangement on Tosylmethyl Isocyanide Derivatives

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 pro...

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Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (13), p.3388-3391
Main Authors: Coppola, Anna, Sánchez-Alonso, Patricia, Sucunza, David, Burgos, Carolina, Alajarín, Ramón, Alvarez-Builla, Julio, Mosquera, Marta E. G, Vaquero, Juan J
Format: Article
Language:English
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Summary: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–cyanide interconversion.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401433x