Tetrahedron letters

A silver-catalyzed Büchner reaction

CJ Lovely, RG Browning, V Badarinarayana…

Index: Lovely, Carl J.; Browning, R. Greg; Badarinarayana, Vivek; Dias, H.V. Rasika Tetrahedron Letters, 2005 , vol. 46, # 14 p. 2453 - 2455

Full Text: HTML

Citation Number: 47

Abstract

A silver scorpionate complex, derived from the highly fluorinated [HB (3, 5-(CF3) 2Pz) 3]−, catalyzes the addition of ethyl diazoacetate to benzene rings, providing norcaradienes, which undergo electrocyclization to provide the corresponding cycloheptatriene. These reactions are surprisingly selective for addition to the aromatic moiety rather than C–H insertion.