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Electrochemical Ruthenium-Catalyzed C–H Hydroxylation of Amine Derivatives in Aqueous Acid

https://doi.org/10.1021/acs.orglett.0c01313

Robinson, Sophia G. ; Mack, James B. ; Alektiar, Sara N. ; Du Bois, J. ; Sigman, Matthew S. ( May 2020 , Organic Letters)

The development of an electrochemically driven, ruthenium-catalyzed C–H hydroxylation reaction of amine-derived substrates bearing tertiary C–H bonds is described. The reaction is performed under constant current electrolysis in a divided cell to afford alcohol products in yields comparable to those of our previously reported process, which requires the use of stoichiometric H5IO6 for catalytic turnover. With aqueous acid as solvent, the cathodic electrode reaction simply involves the reduction of protons to evolve hydrogen gas. The optimized protocol offers a convenient, efficient, and atom-economical method for sp3-C–H bond oxidation.
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Mechanistic Study of Ruthenium-Catalyzed C–H Hydroxylation Reveals an Unexpected Pathway for Catalyst Arrest

https://doi.org/10.1021/jacs.8b10950

Mack, James B. ; Walker, Katherine L. ; Robinson, Sophia G. ; Zare, Richard N. ; Sigman, Matthew S. ; Waymouth, Robert M. ; Du Bois, J. ( January 2019 , Journal of the American Chemical Society)

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Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

https://doi.org/10.1021/acs.jchemed.7b00697

Mack, James B. ; Bedell, T. Aaron ; DeLuca, Ryan J. ; Hone, Graham A. ; Roizen, Jennifer L. ; Cox, Charles T. ; Sorensen, Erik J. ; Du Bois, J. ( October 2018 , Journal of Chemical Education)

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Intermolecular C(sp 3 )−H Amination of Complex Molecules

https://doi.org/10.1002/ange.201713225

Chiappini, Nicholas D. ; Mack, James B. ; Du Bois, J. ( April 2018 , Angewandte Chemie)
Intermolecular C(sp 3 )−H Amination of Complex Molecules

https://doi.org/10.1002/anie.201713225

Chiappini, Nicholas D. ; Mack, James B. C. ; Du Bois, J. ( March 2018 , Angewandte Chemie International Edition)

Abstract
A general and operationally convenient method for intermolecular amination of C(sp³)−H bonds is described. This technology allows for efficient functionalization of complex molecules, including numerous pharmaceutical targets. The combination of pivalonitrile as a solvent, Al₂O₃as an additive, and phenyl sulfamate as a nitrogen source affords differential reaction performance and substrate scope. Mechanistic data strongly implicate a pathway for catalyst decomposition that initiates with solvent oxidation, thus providing rationale for the marked influence of pivalonitrile on this reaction process.

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