Tetrahedron

Insertion of arynes into the carbon–oxygen double bond of amides and its application into the sequential reactions

E Yoshioka, H Miyabe

Index: Yoshioka, Eito; Miyabe, Hideto Tetrahedron, 2012 , vol. 68, # 1 p. 179 - 189

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Citation Number: 29

Abstract

The reaction of arynes, generated from ortho-(trimethylsilyl) aryl triflates, with the CO bond of formamides gave salicylaldehyde derivatives via the formation of formal [2+ 2] adducts. The sequential transformation of arynes into ortho-disubstituted arenes, o-aminoalkylphenols or o-hydroxyalkylphenols, was achieved by one-pot procedure using dialkylzincs.