Synthesis of Allenamides and Structurally Related Compounds by a Gold-Catalyzed Hydride Shift Process

Abstract : A new procedure for the synthesis of allenamides and structurally related compounds is reported. Under gold catalysis, a series of ynamides possessing a benzyloxy group at the propargylic position were efficiently converted into the corresponding allenamides following a 1,5 hydride shift process. The scope of the reaction was shown to be extremely broad allowing the formation of γ‐mono or γ‐disubstituted allenes possessing various functional groups. Notably, and in contrast to previously reported methods, not only N‐allenyl sulfonamido but also urea, phosphonamido and the rarely studied phthalimido, pyrrolo, indolo and carbazolo derivatives could be readily and efficiently accessed.
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Submitted on : Saturday, April 6, 2019 - 11:25:18 AM
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Qing Zhao, Fabien Gagosz. Synthesis of Allenamides and Structurally Related Compounds by a Gold-Catalyzed Hydride Shift Process. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (18), pp.3108-3113. ⟨10.1002/adsc.201700615⟩. ⟨hal-02091717⟩

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