Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202301978
Keywords
Amination; nitrene source; nitroarenes; reductive cyclization; unprotected indolines
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In this study, a metal-free intramolecular benzylic sp(3) C-H amination using aryl nitro compounds as aryl nitrene precursors was disclosed. The organosilicon reagent N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene (Si-DHBP) served as an efficient reductant, enabling the in-situ generation of aryl nitrene species for the direct and metal-free synthesis of unprotected 2-arylindolines from the corresponding nitroarene compounds.
Given the prevalence of molecules containing nitro groups in organic synthesis, innovative methods to expand the reactivity of this functional group are of interest in both industrial and academic settings. In this report, a metal-free intramolecular benzylic sp(3) C-H amination is disclosed using aryl nitro compounds as aryl nitrene precursors. Organosilicon reagent N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene (Si-DHBP) served as an efficient reductant in the transformation, enabling the in situ generation of aryl nitrene species for the direct, metal-free synthesis of unprotected 2-arylindolines from the corresponding nitroarene compounds.
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