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Frontispiece: Iron‐Catalysed Remote C(sp 3 )−H Azidation of O ‐Acyl Oximes and N ‐Acyloxy Imidates Enabled by 1,5‐Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ‐Azido Ketones and β‐Azido Alcohols
Author(s) -
TorresOchoa Rubén O.,
Leclair Alexandre,
Wang Qian,
Zhu Jieping
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201984067
Subject(s) - chemistry , imine , hydrogen atom , redox , atom transfer radical polymerization , carbon atom , medicinal chemistry , carbon fibers , stereochemistry , organic chemistry , catalysis , group (periodic table) , polymerization , materials science , ring (chemistry) , polymer , composite number , composite material
An efficient distal C(sp 3 )−H azidation of both ketoxime esters and N ‐acyloxy imidates for the synthesis of γ‐azido ketones and β‐azido alcohols is reported in the Full Paper by J. Zhu, et al. on page 9477 ff. The artwork represents two essential processes of the proposed mechanism: the 1,5‐hydrogen atom transfer of an imine/imidate radical through a chair‐like transition state, and the iron‐mediated redox azido transfer to the translocated carbon radical.