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8.1.13 Product Subclass 13: Benzyllithium Compounds and (Lithiomethyl)hetarenes

DOI: 10.1055/sos-SD-008-00198

Reed, J. N.Science of Synthesis, (20068329.

General Introduction

Benzyllithium compounds and (lithiomethyl)hetarenes represent a significant portion of the organolithium literature. The first reported use of a simple alkyl organolithium compound as a metalating reagent was, in 1928, the lithiation of 9H-fluorene with ethyllithium to give 9H-fluoren-9-yllithium.[‌1‌] The first example of a (lithiomethyl)hetarene followed soon after in 1931, with the reported lithiation of 2-methylpyridine to give 2-(lithiomethyl)pyridine (Scheme 1).[‌2‌]

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