Direct N-alkyl azidonation of N, N-dialkylarylamines with the iodosylbenzene/trimethylsilyl azide reagent combination

P Magnus, J Lacour, W Weber

文献索引：Magnus, Philip; Lacour, Jerome; Weber, Wolfgang Journal of the American Chemical Society, 1993 , vol. 115, # 20 p. 9347 - 9348

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被引用次数: 72

摘要

While exploring the scope of the 8-azidonation of triisopropylsilyl (TIPS) enol ethers using the reagent combination PhIO/TMSN3, we discovered that triethylamine completely suppressed the formation of the@-azido TIPS enol ether 1, Scheme 1.'Presumably, the more basic triethylamine competes for the electrophilic intermediates more effectively and is oxidized2 by the PhIO/TMSN3 reagent. 3 To ascertain the fate of the amine in this reaction ...