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Hydrazine Derivatives as C-Centered Radical Precursors for C-C Bond Formation Reactions
Elena R Lopat'eva1, Igor B Krylov1, Alexander O Terent'ev1
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia.
Abstract:
Organic monosubstituted hydrazine derivatives (Ar-NHNH2, RC(O)-NHNH2, Alkyl-NHNH2) are synthetically available, atom-efficient and stable sources of C-centered radicals upon oxidation with extrusion of the energetically favorable N2 molecule. This review summarizes the synthetic application of monosubstituted hydrazine derivatives (arylhydrazines, carbazates, acylhydrazides, hydrazine carboxamides and alkylhydrazines) in free-radical C-C bond-forming reactions. The main application directions in this field are (a) alkene difunctionalization, (b) cascade cyclization initiated by the addition of hydrazine-derived C-centered radicals to acrylamides and isonitriles, and (c) CH-functionalization of (hetero)arenes via C-centered radical addition followed by oxidative dehydrogenation (re-aromatization).
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