Exploratory Synthetic Studies of the α-Methoxylation of Amides via Cuprous Ion-Promoted Decomposition of o-Diazobenzamides

…, MC McIntosh, SM Weinreb, M Parvez

Index: Han, Gyoonhee; LaPorte, Matthew G.; McIntosh, Mathias C.; Weinreb, Steven M.; Parvez, Masood Journal of Organic Chemistry, 1996 , vol. 61, # 26 p. 9483 - 9493

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Citation Number: 53

Abstract

A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1, 5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting α-amidyl radical. The transformation produces α-methoxybenzamides 15 in good ...