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Flow Rhodaelectro-Catalyzed Alkyne Annulations by Versatile C-H Activation: Mechanistic Support for Rhodium(III/IV)
W.-J. Kong, L.H. Finger, A.M. Messinis, , J.C.A. Oliveira, L. Ackermann
Published in American Chemical Society
2019
PMID: 31549815
Volume: 141
   
Issue: 43
Pages: 17198 - 17206
Abstract
A flow-metallaelectro-catalyzed C-H activation was realized in terms of robust rhodaelectro-catalyzed alkyne annulations. To this end, a modular electro-flow cell with a porous graphite felt anode was designed to ensure efficient turnover. Thereby, a variety of C-H/N-H functionalizations proved amenable for alkyne annulations with high levels of regioselectivity and functional group tolerance, viable in both an inter- or intramolecular manner. The electro-flow C-H activation allowed easy scale up, while in-operando kinetic analysis was accomplished by online flow-NMR spectroscopy. Mechanistic studies suggest an oxidatively induced reductive elimination pathway on rhodium(III) in an electrocatalytic regime. © 2019 American Chemical Society.
About the journal
JournalData powered by TypesetJournal of the American Chemical Society
PublisherData powered by TypesetAmerican Chemical Society
ISSN00027863