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Benzimidates as <i>gem</i>-Diamidation and Amidoindolyzation Cascade Synthons with a Hydrated Ni<sup>II</sup> Catalyst

Rajesh Nandi, Prakash K. Mandal, Anirban Kayet, Tamalika Bhattachariya, Sukla Ghosh, Dilip K. Maiti

2020Organic Letters17 citationsDOI

Abstract

We contributed a new benzimidate chemistry through moisture-insensitive NiII/NiII-FeIII combo-catalysis for a simultaneous 2–3 bond-forming gem-diamidation and amidoindolyzation cascade reaction to construct symmetrical and unsymmetrical gem-(arylmethylene)amides and indolo(arylmethylene)amides, using emerging benzimidate synthons. The operational simplicity, mild nature, generality, and robustness of the strategy were validated through syntheses of a wide range of new molecules, labile sugar-based chiral compounds, and pharmaceuticals with high yields under the same reaction conditions.

Topics & Concepts

SynthonChemistryCatalysisCascadeCombinatorial chemistryMoleculeOrganic chemistryChromatographyCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesSynthesis and Catalytic Reactions
Benzimidates as <i>gem</i>-Diamidation and Amidoindolyzation Cascade Synthons with a Hydrated Ni<sup>II</sup> Catalyst | Litcius