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Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
Author(s) -
Mo Jiayu,
Müller Thomas,
Oliveira João C. A.,
Demeshko Serhiy,
Meyer Franc,
Ackermann Lutz
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904110
Subject(s) - chemistry , alkyne , propargyl , mössbauer spectroscopy , kinetics , catalysis , ligand (biochemistry) , reaction mechanism , spectroscopy , amide , photochemistry , crystallography , organic chemistry , biochemistry , physics , receptor , quantum mechanics
An iron‐catalyzed C−H/N−H alkyne annulation was realized by using a customizable clickable triazole amide under exceedingly mild reaction conditions. A unifying mechanistic approach combining experiment, spectroscopy, kinetics, and computation provided strong support for facile C−H activation by a ligand‐to‐ligand hydrogen transfer (LLHT) mechanism. Combined Mössbauer spectroscopic analysis and DFT calculations were indicative of high‐spin iron(II) species as the key intermediates in the C−H activation manifold.