Premium
Synthesis of Allenamides and Structurally Related Compounds by a Gold‐Catalyzed Hydride Shift Process
Author(s) -
Zhao Qing,
Gagosz Fabien
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700615
Subject(s) - chemistry , hydride , catalysis , combinatorial chemistry , urea , functional group , organic chemistry , hydrogen , polymer
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.