Highly Selective Insertion of Arynes into a C (sp)− O (sp3) σ Bond

…, D García, D Peña, A Cobas, D Pérez, E Guitián

Index: Laczkowski, Krzysztof Z.; Garcia, Diego; Pena, Diego; Cobas, Agustin; Perez, Dolores; Guitian, Enrique Organic Letters, 2011 , vol. 13, # 5 p. 960 - 963

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Citation Number: 16

Abstract

Arynes react with ethoxyacetylene to afford 2-ethoxyethynylaryl derivatives through a highly chemo-and regioselective formal insertion of the aryne into the C (sp)− O (sp3) bond of the alkyne. Computational studies suggest that the reaction does not proceed through a mechanism initiated by the nucleophilic addition of the oxygen atom to the aryne as previously proposed but by the addition of the triple bond of the alkyne to the aryne.