Electrocatalytic Ketyl-Olefin Cyclization at a Favorable Applied Bias Enabled by a Concerted Proton–Electron Transfer Mediator

Derosa, Joseph; Garrido-Barros, Pablo; Peters, Jonas C.

doi:10.1021/acs.inorgchem.2c00839

Electrocatalytic Ketyl-Olefin Cyclization at a Favorable Applied Bias Enabled by a Concerted Proton–Electron Transfer Mediator

Journal Article · 18 April 2022 · Inorganic Chemistry

DOI:https://doi.org/10.1021/acs.inorgchem.2c00839· OSTI ID:1977888

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Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States

Not provided.

Research Organization:: California Institute of Technology (CalTech), Pasadena, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019136

OSTI ID:: 1977888

Journal Information:: Inorganic Chemistry, Vol. 61, Issue 17; ISSN 0020-1669

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (29)

Recent advances in the chemistry of ketyl radicals Péter, Áron; Agasti, Soumitra; Knowles, Oliver Chemical Society Reviews, Vol. 50, Issue 9 https://doi.org/10.1039/D0CS00358A	journal	January 2021
Stereocontrolled intramolecular ketone-olefin reductive coupling reactions promoted by samarium diiodide Molander, Gary A.; Kenny, Caryn Tetrahedron Letters, Vol. 28, Issue 38 https://doi.org/10.1016/S0040-4039(00)96511-0	journal	January 1987
Intramolecular reductive coupling reactions promoted by samarium diiodide Molander, Gary A.; Kenny, Caryn Journal of the American Chemical Society, Vol. 111, Issue 21 https://doi.org/10.1021/ja00203a027	journal	October 1989
Stereochemical Investigations of Samarium(II) Iodide-Promoted 5-Exo and 6-Exo Ketyl-Olefin Radical Cyclization Reactions Molander, Gary A.; McKie, Jeffrey A. The Journal of Organic Chemistry, Vol. 60, Issue 4 https://doi.org/10.1021/jo00109a018	journal	February 1995
Mechanistic Study and Development of Catalytic Reactions of Sm(II) Maity, Sandeepan; Flowers, Robert A. Journal of the American Chemical Society, Vol. 141, Issue 7 https://doi.org/10.1021/jacs.8b13119	journal	January 2019
Samarium(II)-Iodide-Mediated Cyclizations in Natural Product Synthesis Edmonds, David J.; Johnston, Derek; Procter, David J. Chemical Reviews, Vol. 104, Issue 7 https://doi.org/10.1021/cr030017a	journal	May 2004
Samarium Diiodide Mediated Reactions in Total Synthesis Nicolaou, K. C.; Ellery, Shelby P.; Chen, Jason S. Angewandte Chemie International Edition, Vol. 48, Issue 39 https://doi.org/10.1002/anie.200902151	journal	September 2009
Proton-Coupled Electron Transfer Weinberg, David R.; Gagliardi, Christopher J.; Hull, Jonathan F. Chemical Reviews, Vol. 112, Issue 7 https://doi.org/10.1021/cr200177j	journal	April 2012
PROTON-COUPLED ELECTRON TRANSFER: A Reaction Chemist's View Mayer, James M. Annual Review of Physical Chemistry, Vol. 55, Issue 1 https://doi.org/10.1146/annurev.physchem.55.091602.094446	journal	June 2004
Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities Miller, David C.; Tarantino, Kyle T.; Knowles, Robert R. Topics in Current Chemistry, Vol. 374, Issue 3 https://doi.org/10.1007/s41061-016-0030-6	journal	May 2016
Proton-Coupled Electron Transfer in the Reduction of Carbonyls by Samarium Diiodide–Water Complexes Chciuk, Tesia V.; Anderson, William R.; Flowers, Robert A. Journal of the American Chemical Society, Vol. 138, Issue 28 https://doi.org/10.1021/jacs.6b05879	journal	July 2016
Interplay between Substrate and Proton Donor Coordination in Reductions of Carbonyls by SmI ₂ –Water Through Proton-Coupled Electron-Transfer Chciuk, Tesia V.; Anderson, William R.; Flowers, Robert A. Journal of the American Chemical Society, Vol. 140, Issue 45 https://doi.org/10.1021/jacs.8b08890	journal	October 2018
Catalytic Ketyl-Olefin Cyclizations Enabled by Proton-Coupled Electron Transfer Tarantino, Kyle T.; Liu, Peng; Knowles, Robert R. Journal of the American Chemical Society, Vol. 135, Issue 27 https://doi.org/10.1021/ja404342j	journal	June 2013
Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols Fava, Eleonora; Nakajima, Masaki; Nguyen, Anh L. P. The Journal of Organic Chemistry, Vol. 81, Issue 16 https://doi.org/10.1021/acs.joc.6b01006	journal	June 2016
Electroorganic chemistry. VIII. Intramolecular cycloaddition of nonconjugate olefinic ketones to form cyclic tertiary alcohols Shono, Tatsuya; Mitani, Michiharu Journal of the American Chemical Society, Vol. 93, Issue 20 https://doi.org/10.1021/ja00749a068	journal	October 1971
Electroorganic chemistry. 31. Reductive cyclization of nonconjugated olefinic ketones to cyclic tertiary alcohols Shono, Tatsuya; Nishiguchi, Ikuzo; Ohmizu, Hiroshi Journal of the American Chemical Society, Vol. 100, Issue 2 https://doi.org/10.1021/ja00470a031	journal	January 1978
Intramolecular electroreductive cyclization of heteroatom-containing non-conjugated enones and ynones Goda, Satoshi; Yamada, Kouji; Yamamoto, Yoshimasa Journal of Electroanalytical Chemistry, Vol. 545 https://doi.org/10.1016/S0022-0728(03)00082-2	journal	March 2003
Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance Yan, Ming; Kawamata, Yu; Baran, Phil S. Chemical Reviews, Vol. 117, Issue 21 https://doi.org/10.1021/acs.chemrev.7b00397	journal	October 2017
Electroreductive Olefin–Ketone Coupling Hu, Pengfei; Peters, Byron K.; Malapit, Christian A. Journal of the American Chemical Society, Vol. 142, Issue 50 https://doi.org/10.1021/jacs.0c11214	journal	December 2020
A molecular mediator for reductive concerted proton-electron transfers via electrocatalysis Chalkley, Matthew J.; Garrido-Barros, Pablo; Peters, Jonas C. Science, Vol. 369, Issue 6505 https://doi.org/10.1126/science.abc1607	journal	August 2020
Electrocatalytic Reduction of C–C π-Bonds via a Cobaltocene-Derived Concerted Proton–Electron Transfer Mediator: Fumarate Hydrogenation as a Model Study Derosa, Joseph; Garrido-Barros, Pablo; Peters, Jonas C. Journal of the American Chemical Society, Vol. 143, Issue 25 https://doi.org/10.1021/jacs.1c03335	journal	June 2021
Mechanisms of solvolytic elimination reactions of tertiary substrates: stereospecific 1,2-elimination reactions Meng, Qingshui; Thibblin, Alf Journal of the Chemical Society, Perkin Transactions 2, Issue 7 https://doi.org/10.1039/a901296f	journal	January 1999
Dual Lewis Acid/Photoredox-Catalyzed Addition of Ketyl Radicals to Vinylogous Carbonates in the Synthesis of 2,6-Dioxabicyclo[3.3.0]octan-3-ones Foy, Nicholas J.; Forbes, Katherine C.; Crooke, Anne Marie Organic Letters, Vol. 20, Issue 18 https://doi.org/10.1021/acs.orglett.8b02442	journal	September 2018
Multielectron, Multistep Molecular Catalysis of Electrochemical Reactions: Benchmarking of Homogeneous Catalysts Costentin, Cyrille; Savéant, Jean-Michel ChemElectroChem, Vol. 1, Issue 7 https://doi.org/10.1002/celc.201300263	journal	June 2014
Electrolytic Reduction of Organic Compounds. Popp, Frank D.; Schultz, Harry P. Chemical Reviews, Vol. 62, Issue 1 https://doi.org/10.1021/cr60215a002	journal	February 1962
Study of Steric Effects by Electron Spin Resonance Spectroscopy and Polarography. Substituted Nitrobenzenes and Nitroanilines Geske, David H.; Ragle, John L.; Bambenek, Mark A. Journal of the American Chemical Society, Vol. 86, Issue 6 https://doi.org/10.1021/ja01060a004	journal	March 1964
Mechanisms of Inhibitory and Regulatory Effects of Methylenedioxyphenyl Compounds on Cytochrome P450-Dependent Drug Oxidation Murray, Michael Current Drug Metabolism, Vol. 1, Issue 1 https://doi.org/10.2174/1389200003339270	journal	July 2000
A Theoretical and Experimental Investigation of the Kinetics of Ring Closure of the 3-Methyl-3-azahex-5-enyl Radical Della, Ew; Knill, Am Australian Journal of Chemistry, Vol. 48, Issue 12 https://doi.org/10.1071/CH9952047	journal	January 1995
Theoretical Study of Factors Controlling Rates of Cyclization of Radical Intermediates from Diallylamine and Diallylammonium Monomers in Radical Polymerizations Tüzün, N. S.; Aviyente, V.; Houk, K. N. The Journal of Organic Chemistry, Vol. 67, Issue 15 https://doi.org/10.1021/jo0256639	journal	June 2002

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