Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations

Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assembl...

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Published inAngewandte Chemie International Edition Vol. 60; no. 12; pp. 6419 - 6424
Main Authors Wang, Yulei, Oliveira, João C. A., Lin, Zhipeng, Ackermann, Lutz
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 15.03.2021
Wiley Subscription Services, Inc
John Wiley and Sons Inc
EditionInternational ed. in English
Subjects
[5+2] cycloaddition
Alkynes
Anodizing
benzoxepine
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Communication
Communications
C−H activation
Electrochemistry
electrooxidative annulation
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Rhodium
Science & Technology
Substrates
Transition metals
ELECTROSYNTHESIS
electrochemistry
benzoxepine
electrooxidative annulation
OXIDATIVE ANNULATION
CLEAVAGE
STRATEGIES
[5+2] cycloaddition
BODIPY DYES
FUNCTIONALIZATION
ANILINES
REGIOSELECTIVE SYNTHESIS
H activation
C&#8722
CYCLIZATION
C−H activation
Online AccessGet full text

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Abstract Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a benzoxepine‐coordinated rhodium(I) sandwich complex as the catalyst resting state, which was re‐oxidized to rhodium(III) by anodic oxidation. Electrochemical rhodium‐catalyzed [5+2] cycloadditions to assemble seven‐membered benzoxepines have been accomplished guided by detailed mechanistic insights.
AbstractList Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a benzoxepine‐coordinated rhodium(I) sandwich complex as the catalyst resting state, which was re‐oxidized to rhodium(III) by anodic oxidation.
Electrooxidative annulations involving mild transition metal-catalyzed C-H activation have emerged as a transformative strategy for the rapid construction of five- and six-membered heterocycles. In contrast, we herein describe the first electrochemical metal-catalyzed [5+2] cycloadditions to assemble valuable seven-membered benzoxepine skeletons by C-H/O-H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a benzoxepine-coordinated rhodium(I) sandwich complex as the catalyst resting state, which was re-oxidized to rhodium(III) by anodic oxidation.
Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a benzoxepine‐coordinated rhodium(I) sandwich complex as the catalyst resting state, which was re‐oxidized to rhodium(III) by anodic oxidation. Electrochemical rhodium‐catalyzed [5+2] cycloadditions to assemble seven‐membered benzoxepines have been accomplished guided by detailed mechanistic insights.
Abstract Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a benzoxepine‐coordinated rhodium(I) sandwich complex as the catalyst resting state, which was re‐oxidized to rhodium(III) by anodic oxidation.
Author Oliveira, João C. A.
Lin, Zhipeng
Wang, Yulei
Ackermann, Lutz
AuthorAffiliation 1 Institut für Organische und Biomolekulare Chemie, and Wöhler Research Institute for Sustainable Chemistry Georg-August-Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany
AuthorAffiliation_xml – name: 1 Institut für Organische und Biomolekulare Chemie, and Wöhler Research Institute for Sustainable Chemistry Georg-August-Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany
Author_xml – sequence: 1
  givenname: Yulei
  surname: Wang
  fullname: Wang, Yulei
  organization: Georg-August-Universität Göttingen
– sequence: 2
  givenname: João C. A.
  surname: Oliveira
  fullname: Oliveira, João C. A.
  organization: Georg-August-Universität Göttingen
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  givenname: Zhipeng
  surname: Lin
  fullname: Lin, Zhipeng
  organization: Georg-August-Universität Göttingen
– sequence: 4
  givenname: Lutz
  orcidid: 0000-0001-7034-8772
  surname: Ackermann
  fullname: Ackermann, Lutz
  email: Lutz.Ackermann@chemie.uni-goettingen.de
  organization: Georg-August-Universität Göttingen
BackLink https://www.ncbi.nlm.nih.gov/pubmed/33471952$$D View this record in MEDLINE/PubMed
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Issue 12
Keywords ELECTROSYNTHESIS
electrochemistry
benzoxepine
electrooxidative annulation
OXIDATIVE ANNULATION
CLEAVAGE
STRATEGIES
[5+2] cycloaddition
BODIPY DYES
FUNCTIONALIZATION
ANILINES
REGIOSELECTIVE SYNTHESIS
H activation
C&#8722
CYCLIZATION
C−H activation
Language English
License Attribution-NonCommercial
2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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.
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Snippet Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of...
Electrooxidative annulations involving mild transition metal-catalyzed C-H activation have emerged as a transformative strategy for the rapid construction of...
Abstract Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid...
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SubjectTerms [5+2] cycloaddition
Alkynes
Anodizing
benzoxepine
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Communication
Communications
C−H activation
Electrochemistry
electrooxidative annulation
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Rhodium
Science & Technology
Substrates
Transition metals
Title Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202016895
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000615932800001
https://www.ncbi.nlm.nih.gov/pubmed/33471952
https://www.proquest.com/docview/2497948832
https://search.proquest.com/docview/2479708344
https://pubmed.ncbi.nlm.nih.gov/PMC7986427
Volume 60
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