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

Wang, Yulei ; Oliveira, João C. A. ; Lin, Zhipeng ; Ackermann, Lutz

Angewandte Chemie International Edition, 2021-03, Vol.60 (12), p.6419-6424 [Peer Reviewed Journal]

Germany: Wiley Subscription Services, Inc

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Title:
Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations
Author: Wang, Yulei ; Oliveira, João C. A. ; Lin, Zhipeng ; Ackermann, Lutz
Subjects: [5+2] cycloaddition ; Alkynes ; Anodizing ; benzoxepine ; Catalysts ; Chemical reactions ; Communication ; Communications ; C−H activation ; Electrochemistry ; electrooxidative annulation ; Oxidants ; Oxidation ; Oxidizing agents ; Rhodium ; Substrates ; Transition metals
Is Part Of: Angewandte Chemie International Edition, 2021-03, Vol.60 (12), p.6419-6424
Notes: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Description: 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.
Publisher: Germany: Wiley Subscription Services, Inc
Language: English

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

Wang, Yulei ; Oliveira, João C. A. ; Lin, Zhipeng ; Ackermann, Lutz

Germany: Wiley Subscription Services, Inc

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