Generation and Aerobic Oxidation of Azavinyl Captodative Radicals
Shubhangi Aggarwal,
William J. Richards,
Valery V. Fokin
Abstract:We describe a cascade reaction that selectively incorporates oxygen into the carbon−carbon backbone of alkynes using air as the source. The process starts by lithiating readily available, electron-deficient 1,2,3-triazoles, resulting in an amphoteric lithium ketenimine intermediate. This intermediate can react with both electrophiles and nucleophiles. Under the conditions outlined in this study, we generate azavinyl radicals, which are a rare subset of captodative radicals. When exposed to atmospheric oxygen, … Show more
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