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DTBP/TBHP-Promoted Hydroacylation of Unactivated Alkenes†

Research paper by Huei‐Shu Jhuang, Dr. Daggula Mallikarjuna Reddy, Te‐Hsuan Chen, Prof. Dr. Chin‐Fa Lee

Indexed on: 29 Oct '16Published on: 28 Oct '16Published in: Asian Journal of Organic Chemistry



Abstract

Di-tert-butyl peroxide (DTBP)-promoted intermolecular hydroacylation reaction of alkenes with aromatic aldehydes that provides ketones is described. In this study, 4-chromanones were formed when 2-(allyloxy)benzaldehydes were treated with tert-butyl hydroperoxide (TBHP). The reactions were performed under solvent- and metal-free conditions. Reactions proceeded through the generation of acyl radicals, followed by the reaction with alkenes. Remarkably, not only terminal alkenes but also internal alkenes could serve as the starting materials for intramolecular hydroacylation reaction.