Abstract
This chapter discusses the methods to obtain the various thienyllithium derivatives. Thienyllithium derivatives are of much greater importance in syntheses than phenyllithium derivatives. This is due to the easy and convenient preparation of 2-thienyllithium derivatives by metalation of thiophene with butyllithium in ether at reflux temperature or lower. Other metalating reagents such as lithium diisopropylamide, which is especially useful if the thiophene ring also carries iodine-, bromine- or carbonyl-containing substituents, can also be used. This has opened the possibility to prepare a great variety of disubstituted thiophenes, some of them in one-pot procedure. However, one should always be aware of the possibility of rearrangement reactions, when lithium does not substitute the most acidic hydrogen. The different functionalized thiophenes obtained through reactions with a manifold of electrophiles are also treated briefly.
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