Organolithium compounds with aromatic rings

Other unconventional methods were also developed for introducing substituents into the phenyl ring of the 5-aryltetrazoles. Reaction of organolithium compounds (BuLi, PhLi, /)-tolyllithium, 1-naphthyllithium, etc.) with 2-cumyl-5-(2-methoxyphenyl)tetrazole 330 (in hexane, 23 °C, 4.5 h) led to corresponding products of nucleophilic aromatic substitution such as 331 and 332 in 47-90% yields <1999JOC9301>. 

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