Formation of 1,3,5-Trilithiobenzene and Its Conversion to the Corresponding Magnesium, Mercury, and Tin Derivatives

Abstract

Whereas the halogen−metal exchange approach from 1,3,5-tribromobenzene (3) to 1,3,5-trilithiobenzene (1) was unsuccessful, 1 was synthesized in high yield (about 80%) by reaction of 3 with LiDBB (lithium 4,4‘-di-tert-butylbiphenyl). Compound 1 was used as the starting material for the preparation of other symmetrical trimetalated benzenes, 1,3,5-C6H3(MgBr)3 (20), 1,3,5-C6H3(SnMe3)3 (23), and 1,3,5-C6H3(HgBr)3 (26), by reaction with the corresponding metal halides.