Benzimidates as gem-Diamidation and Amidoindolyzation Cascade Synthons with a Hydrated NiII Catalyst

• Published in: Organic letters Vol. 22; no. 9; pp. 3474 - 3478
• Main Authors: Nandi, Rajesh, Mandal, Prakash K, Kayet, Anirban, Bhattachariya, Tamalika, Ghosh, Sukla, Maiti, Dilip K
• Format: Journal Article
• Language: English
• Published: American Chemical Society 01-05-2020
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.0c00928

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.