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PhI(OAc) 2 ‐Promoted 1,2‐Diaza‐Cope Rearrangement of β,γ‐Unsaturated Hydrazones with Acetate/H 2 O: Access to Diacyl/Acyl N ‐Allylhydrazines
Author(s) -
Fang ZhuoYue,
Qi Lin,
Song JinYan,
Ren PeiXing,
Hou CongYing,
Ji ShiChao,
Wang LiJing,
Li Wei
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000875
Subject(s) - chemistry , cope rearrangement , radical , rearrangement reaction , medicinal chemistry , hydrazone , reaction mechanism , reaction conditions , stereochemistry , organic chemistry , catalysis
A novel metal‐free methodology for the synthesis of diacyl/acyl N ‐allylhydrazines based on PhI(OAc) 2 ‐promoted 1,2‐diaza‐Cope rearrangement reaction of β,γ‐unsaturated hydrazones with acetate/H 2 O has been described. This cascade reaction works efficiently under mild conditions. A possible mechanism involving hydrazonyl radicals and N–I(III) intermediates of β,γ‐unsaturated hydrazones is proposed.