Non-Deprotonating Methodologies for Organolithium Reagents Starting from Non-Halogenated Materials. Part 1: Carbon – Heteroatom Bond Cleavage

David      Guijarro; Isidro      M. Pastor; Miguel      Yus

doi:10.2174/138527211794072560

Abstract

The publications appeared in the last eleven years on the topic of the preparation of organolithium reagents by nondeprotonating methodologies and starting from non-halogenated substrates have been covered in the present revision. In this part, the carbon – heteroatom bond cleavage under reductive conditions has been considered, carbon – oxygen and carbon – sulfur bond cleavages (both in acyclic or cyclic systems) being of paramount importance. Additionally, other bond scissions, such as carbon – nitrogen, carbon – phosphorous, carbon – fluorine, carbon – silicon, carbon – selenium and carbon – tellurium bonds are recorded.

Keywords: Lithium, organolithium, arene-catalysed lithiation, carbon, –, heteroatom bond cleavage, reductive cleavage, heterocycle reductive ring opening, deprotonation, carbolithiation, formylphenyllithiums, chlorotrimethylsilane, DTBB, Dianions, 2,3-benzodihydrofuran, TMEDA, Dinaphthooxepine, lithiation-SE reaction, LiDTBB, PhSLi, Poly(lithiomethyl)silanes, LDMAN, homoallyllithium reagent, dihydrodibenzothiepine, Fritsch-Buttenberg-Wiechell rearrangement, allyllithium, N-methyldibenzoazepine, tetrahydropyran, Brook rearrangement, oxy-Cope rearrangement, sec-butyllithium