Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations

A ruthenium‐catalyzed electrochemical dehydrogenative annulation reaction of imidazoles with alkynes has been established, enabling the preparation of various bridgehead N‐fused [5,6]‐bicyclic heteroarenes through regioselective electrochemical C−H/N−H annulation without chemical metal oxidants. Nov...

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Autores principales: Yang, Long, Steinbock, Ralf, Scheremetjew, Alexej, Kuniyil, Rositha, Finger, Lars H., Messinis, Antonis M., Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317209/
https://www.ncbi.nlm.nih.gov/pubmed/32129528
http://dx.doi.org/10.1002/anie.202000762
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author Yang, Long
Steinbock, Ralf
Scheremetjew, Alexej
Kuniyil, Rositha
Finger, Lars H.
Messinis, Antonis M.
Ackermann, Lutz
author_facet Yang, Long
Steinbock, Ralf
Scheremetjew, Alexej
Kuniyil, Rositha
Finger, Lars H.
Messinis, Antonis M.
Ackermann, Lutz
author_sort Yang, Long
collection PubMed
description A ruthenium‐catalyzed electrochemical dehydrogenative annulation reaction of imidazoles with alkynes has been established, enabling the preparation of various bridgehead N‐fused [5,6]‐bicyclic heteroarenes through regioselective electrochemical C−H/N−H annulation without chemical metal oxidants. Novel azaruthenabicyclo[3.2.0]heptadienes were fully characterized and identified as key intermediates. Mechanistic studies are suggestive of an oxidatively induced reductive elimination pathway within a ruthenium(II/III) regime.
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spelling pubmed-73172092020-06-30 Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations Yang, Long Steinbock, Ralf Scheremetjew, Alexej Kuniyil, Rositha Finger, Lars H. Messinis, Antonis M. Ackermann, Lutz Angew Chem Int Ed Engl Research Articles A ruthenium‐catalyzed electrochemical dehydrogenative annulation reaction of imidazoles with alkynes has been established, enabling the preparation of various bridgehead N‐fused [5,6]‐bicyclic heteroarenes through regioselective electrochemical C−H/N−H annulation without chemical metal oxidants. Novel azaruthenabicyclo[3.2.0]heptadienes were fully characterized and identified as key intermediates. Mechanistic studies are suggestive of an oxidatively induced reductive elimination pathway within a ruthenium(II/III) regime. John Wiley and Sons Inc. 2020-05-12 2020-06-26 /pmc/articles/PMC7317209/ /pubmed/32129528 http://dx.doi.org/10.1002/anie.202000762 Text en © 2020 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-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Yang, Long
Steinbock, Ralf
Scheremetjew, Alexej
Kuniyil, Rositha
Finger, Lars H.
Messinis, Antonis M.
Ackermann, Lutz
Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title_full Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title_fullStr Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title_full_unstemmed Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title_short Azaruthena(II)‐bicyclo[3.2.0]heptadiene: Key Intermediate for Ruthenaelectro(II/III/I)‐catalyzed Alkyne Annulations
title_sort azaruthena(ii)‐bicyclo[3.2.0]heptadiene: key intermediate for ruthenaelectro(ii/iii/i)‐catalyzed alkyne annulations
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317209/
https://www.ncbi.nlm.nih.gov/pubmed/32129528
http://dx.doi.org/10.1002/anie.202000762
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