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Efficient and Divergent Synthesis of alpha-Halogenated Amides and Esters by Double Electrophilic Activation of Ynamides

par Thilmany, Pierre ;Evano, Gwilherm
Référence Angewandte Chemie International Edition in English, 59, page (242-246)
Publication Publié, 2020-01-01

Article révisé par les pairs

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Résumé :

An efficient and modular entry to alpha-halogenated amides and esters is reported. This reaction is based on an underrated double electrophilic activation of ynamides sequentially involving highly reactive activated keteniminium and iminium ions. Upon simple reaction with HCl and an electrophilic halogenation reagent in the presence of water or an alcohol, a broad range of ynamides can be transformed, in a highly divergent manner, to alpha-halo-amides and esters with high efficiency and under mild conditions.