Single Electron Transfer (SET) oxidation is a process that involves the removal of a single electron from a carbanion, resulting in the formation of an electron-deficient carbon-centered radical, and subsequent cyclization reaction with alkene, alkyne, or aryl group. This strategy has been playing a significant role in achieving the stereoselective synthesis of structurally complex and biologically important carbo- and heterocyclic ring systems.1
Using SET oxidative cyclization of carbanion as a key strategy, our group has developed a novel one-pot method for the synthesis of structurally intriguing cyclopropane-fused bicyclic amidine. Recently, the same protocol has been further exploited towards the one-pot synthesis of 2-amino indole under mild conditions (Scheme 1).2
Scheme 1. One-pot syntheses of cyclopropane-fused bicyclic amidine and 2-aminoindole.
In this presentation, the synthesis of complex organic frameworks using different transition metal salts as SET oxidants will be discussed. Besides, the application of photo-SET oxidative cyclization as well as metal-free SET oxidative cyclization involving electrochemical radicals will be discussed.
References:
1. Zhang, N.; Rosen, B. M.; Samanta, S. R.; Percec, V.; Chem. Rev., 2014, 114, 5848−5958 (b) Yan, M.; Lo, J. C.; Edwards, J. C.; Baran, P. S.; J. Am. Chem. Soc., 2016, 138, 12692. (c) Li, Y.; Feng, J.; Huang, F.; Baell, J. B.; Chem. Eur. J., 2023, 29, e202301017.
2. (a) Veeranna, K. D.; Das. K. K.; Baskaran, S.; Angew. Chem. Int. Ed., 2017, 56, 16197–16201. (b) Srivastava, A.; Palanivel, L.; Baskaran, S.; Chem. Eur. J., 2023, 29, e202300828.