Tetrahedron

Arylation of lawsone through BF 3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes

…, E Malamidou-Xenikaki, H Skouros, S Spyroudis…

Index: Glinis, Elias; Malamidou-Xenikaki, Elizabeth; Skouros, Haris; Spyroudis, Spyros; Tsanakopoulou, Maria Tetrahedron, 2010 , vol. 66, # 31 p. 5786 - 5792

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Citation Number: 8

Abstract

Phenyliodonium ylide of lawsone, activated by BF3· Et2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1, 4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3· Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction.