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Copper‐Catalyzed Cyclization and Azidation of γ,δ‐Unsaturated Ketone O‐Benzoyl Oximes
Author(s) -
Su Hailin,
Li Weifei,
Xuan Zhaoli,
Yu Wei
Publication year - 2015
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.201400681
Subject(s) - chemistry , ketone , catalysis , oxime , acetonitrile , copper , medicinal chemistry , azide , intramolecular force , cleavage (geology) , polymer chemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
An intramolecular imination/azidation sequence has been realized through the tetrakis(acetonitrile)copper(I) hexafluorophophate [Cu(CH 3 CN) 4 PF 6 ]‐catalyzed reaction of γ,δ‐unsaturated ketone O ‐benzoyl oximes with trimethylsilyl azide (TMSN 3 ). The reaction proceeds via the copper‐mediated NO cleavage and subsequent CN forming 5‐ exo cyclization. The thus formed intermediate is then azidated to afford the corresponding dihydropyrrole product. Preliminary mechanistic investigations suggest that the cyclization step does not involve a radical intermediate.