The Journal of organic chemistry

In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles

I Popov, HQ Do, O Daugulis

Index: Popov, Ilya; Do, Hien-Quang; Daugulis, Olafs Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8309 - 8313

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Citation Number: 38

Abstract

A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, t BuOLi base is required. Arenes with DMSO p K a values of 35 or less are reactive.