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Molecular Oxygen Mediated Radical Dicarbofunctionalization of Olefin with Aldehyde

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journal contribution
posted on 26.04.2018 by Promita Biswas, Joyram Guin
Herein we present a metal- and peroxide-free method for the synthesis of sterically hindered amides bearing an all-carbon quaternary stereogenic center at the α-position via a one-pot alkylation/aryl-migration/desulfonylation radical cascade. The novel process is developed employing readily available and inexpensive aldehyde as an alkyl radical precursor and O2 as the sole oxidant. The method features a broad substrate scope, operational simplicity, convenient reagents, and scalability. A radical chain mechanism that is initiated by O2 is proposed for the process.