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10.21.1.4.1.1.1.1 Formation of C-Lithium

DOI: 10.1055/sos-SD-110-00324

Stanforth, S. P.Science of Synthesis Knowledge Updates, (2014326.

The lithiation of thieno[3,2-b]thiophenes by lithium–hydrogen exchange is a valuable synthetic reaction and has been extensively exploited as a route for the functionalization of these heterocycles because of their importance in materials chemistry (Table 1). Typically, monolithiation is achieved by treating the thieno[3,2-b]thiophene derivative with a slight excess of butyllithium or, in the case of brominated thieno[3,2-b]thiophenes, lithium diisopropylamide. Dilithiation reactions are also feasible when 2 equivalents of the lithiating agent are employed. The organolithium intermediates are then reacted with appropriate electrophiles and these reactions, together with experimental procedures for generating the lithiated heterocycles, are discussed in Section 10.21.1.4.1.3 (substitution of metals). Lithiated hetaryl[3,2-b]hetarenes can be quenched with deuterium oxide thus demonstrating the efficiency of the metalation process as illustrated by the quantitative incorporation of deuterium into 3,6-dimethylthieno[3,2-b]thiophen-2-yllithium.[‌75‌]

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