Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes

作者：Glinis Elias; Malamidou Xenikaki Elizabeth^*; Skouros Hans; Spyroudis Spyros; Tsanakopoulou Maria

来源：Tetrahedron, 2010, 66(31): 5786-5792.

DOI：10.1016/j.tet.2010.04.120

• Lawsone
• Phenyliodonium ylide
• Arylation
• Hydroxyquinones
• Coupling

Phenyliodonium ylide of lawsone, activated by BF3 center dot 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 center dot Et2O-activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction.

• 出版日期2010-7-31