Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation

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 l...

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Detalles Bibliográficos
Autores principales: Mo, Jiayu, Müller, Thomas, Oliveira, João C. A., Demeshko, Serhiy, Meyer, Franc, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187192/
https://www.ncbi.nlm.nih.gov/pubmed/31207070
http://dx.doi.org/10.1002/anie.201904110
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author Mo, Jiayu
Müller, Thomas
Oliveira, João C. A.
Demeshko, Serhiy
Meyer, Franc
Ackermann, Lutz
author_facet Mo, Jiayu
Müller, Thomas
Oliveira, João C. A.
Demeshko, Serhiy
Meyer, Franc
Ackermann, Lutz
author_sort Mo, Jiayu
collection PubMed
description 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.
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spelling pubmed-71871922020-04-28 Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation Mo, Jiayu Müller, Thomas Oliveira, João C. A. Demeshko, Serhiy Meyer, Franc Ackermann, Lutz Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2019-07-30 2019-09-09 /pmc/articles/PMC7187192/ /pubmed/31207070 http://dx.doi.org/10.1002/anie.201904110 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Mo, Jiayu
Müller, Thomas
Oliveira, João C. A.
Demeshko, Serhiy
Meyer, Franc
Ackermann, Lutz
Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title_full Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title_fullStr Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title_full_unstemmed Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title_short Iron‐Catalyzed C−H Activation with Propargyl Acetates: Mechanistic Insights into Iron(II) by Experiment, Kinetics, Mössbauer Spectroscopy, and Computation
title_sort iron‐catalyzed c−h activation with propargyl acetates: mechanistic insights into iron(ii) by experiment, kinetics, mössbauer spectroscopy, and computation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187192/
https://www.ncbi.nlm.nih.gov/pubmed/31207070
http://dx.doi.org/10.1002/anie.201904110
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