(58) Liu, J.; Rong, J.; Wood, D. P.; Wang, Y.; Liang, S. H.*; Lin, S.* “Co-Catalyzed Hydrofluorination of Alkenes: Photocatalytic Method Development and Electroanalytical Mechanistic Investigation.” J. Am. Chem. Soc. 2024, 146, 4380–4392. DOI: 10.1021/jacs.3c10989 [html]
(57) Wang, Y.; Deng, J.; Ressler, A. J.; Lin, S.* “Electroreductive Radical Addition–Polar Cyclization Cascade to Access Cycloalkanes.” Org. Lett. 2024, 26, 116–121. DOI: 10.1021/acs.orglett.3c03722 [html]
(56) Zhang, W.; Guan, W.; Wang, Y.; Lin, S.; See, K. A.* “Enabling Al Sacrificial Anodes in Tetrahydrofuran Electrolytes for Reductive Electrosynthesis.” Chem. Sci. 2023, 14, 13108–13118. DOI: 10.1039/D3SC04725C [html]
(55) Rein, J.; Zacate, S. B.; Mao, K.; Lin, S.* “A Tutorial on Asymmetric Electrocatalysis.” Chem. Soc. Rev. 2023, 52, 8106–8125. DOI: 10.1039/D3CS00511A [html]
(54) Lu, L.; Wang, Y.; Zhang, W.; Zhang, W.; See, K. A.; Lin, S.* “Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes.” J. Am. Chem. Soc. 2023, 145, 22298–22304. DOI: 10.1021/jacs.3c06794 [html]
(53) Ju, M.; Lu, Z.; Novaes, L. F. T.; Martinez Alvarado, J. I.; Lin, S.* “Frustrated Radical Pairs in Organic Synthesis.” J. Am. Chem. Soc. 2023, 145, 19478–19489. DOI: 10.1021/jacs.3c07070 [html]
(52) Boucher, D. G.; Pendergast, A. D.; Wu, X.; Nguyen, Z. A.; Jadhav, R. G.; Lin, S.; White, H. S.; Minteer, S. D.* “Unraveling Hydrogen Atom Transfer Mechanisms with Voltammetry: Oxidative Formation and Reactivity of Cobalt Hydride.” J. Am. Chem. Soc. 2023, 145, 17665–17677. DOI: 10.1021/jacs.3c03815 [html]
(51) Zhang, W.; Gu, C.; Wang, Y.; Ware, S. D.; Lu, L.; Lin, S.; Qi, Y.; See, K. A.* “Improving the Mg Sacrificial Anode in Tetrahydrofuran for Synthetic Electrochemistry by Tailoring Electrolyte Composition.” JACS Au 2023, 3, 2280–2290. DOI: 10.1021/jacsau.3c00305 [html]
(50) Guan, W.; Chang, Y.; Lin, S.* “Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds.” J. Am. Chem. Soc. 2023, 145, 16966–16972. DOI: 10.1021/jacs.3c03418 [html]
Highlighted in ChemistryViews
Selected as an item of interest to process R&D chemists and engineers by OPR&D
(49) Lu, Z.; Ju, M.; Wang, Y.; Meinhardt, J. M.; Martinez Alvarado, J. I.; Villemure, E.; Terrett, J. A.; Lin, S.* “Regioselective Aliphatic C–H Functionalization Using Frustrated Radical Pairs.” Nature 2023, 619, 514–520. DOI: 10.1038/s41586-023-06131-3 [html] [open access link]
Highlighted in Chem
(48) Yu, P.; Zhang, W.; Lin, S.* “Enantioselective Radical Cascade Cyclization via Ti-Catalyzed Redox Relay.” Tetrahedron Lett. 2023, 125, 154617. DOI: 10.1016/j.tetlet.2023.154617 [html] This paper was invited for a special issue honoring Bill Morandi’s Tetrahedron Young Investigator Award.
(47) Zhang, W.; Guan, W.; Martinez Alvarado, J. I.; Novaes, L. F. T.; Lin, S.* “Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-Based Reactive Intermediates in Organic Synthesis.” ACS Catal. 2023, 13, 8038–8048. DOI: 10.1021/acscatal.3c01174 [html] Invited Viewpoint article
(46) Rein, J.; Rozema, S. D.; Langner, O. C.; Zacate, S. B.; Hardy, M. A.; Siu, J. C.; Mercado, B. Q.; Sigman, M. S.*; Miller, S. J.*; Lin, S.* “Generality-Oriented Optimization of Enantioselective Aminoxyl Radical Catalysis.” Science 2023, 380, 706–712. DOI: 10.1126/science.adf6177 [html]
(45) Guan, W.; Lu, L.; Jiang, Q.; Gittens, A. F.; Wang, Y.; Novaes, L. F. T.; Klausen, R. S.*; Lin, S.* “An Electrochemical Strategy to Synthesize Disilanes and Oligosilanes from Chlorosilanes.” Angew. Chem., Int. Ed. 2023, 62, e202303592. DOI: 10.1002/anie.202303592. [html]
(44) Rein, J.; Meinhardt, J. M.; Hofstra Wahlman, J. L.; Sigman, M. S.*; Lin, S.* “A Physical Organic Approach towards Statistical Modeling of Tetrazole and Azide Decomposition.” Angew. Chem., Int. Ed. 2023, 62, e202218213. DOI: 10.1002/anie.202218213. [html]
(43) Wood, D.; Lin, S.* “Deuterodehalogenation Under Net Reductive or Redox-Neutral Conditions Enabled by Paired Electrolysis.” Angew. Chem., Int. Ed. 2023, 62, e202218858. DOI: 10.1002/anie.202218858. [html]
(42) Sun, G.-Q.; Yu, P.; Zhang, W.; Zhang, W.; Wang, Y.; Liao, L.-L.; Zhang, Z.; Li, L.; Lu, Z.; Yu, D.-G.*; Lin, S.* “Electrochemical reactor dictates site selectivity in N-heteroarene carboxylations.” Nature 2023, 615, 67–72. DOI: 10.1038/s41586-022-05667-0 [html] [open access link]
Highlighted in Chem, Angewandte Chemie, and Science China Chemistry
(41) Tran, V. T.; Kim, N.; Rubel, C. Z.; Wu, X.; Kang, T.; Jankins, T. C.; Li, Z.-Q.; Joannou, M. V.; Ayers, S.; Gembicky, M.; Bailey, J.; Sturgell, E. J.; Sanchez, B. B.; Chen, J. S.; Lin, S.; Eastgate, M. D.; Wisniewski, S. R.; Engle, K. M.* “Structurally Diverse Bench-Stable Nickel(0) Pre-Catalysts: A Practical Toolkit for In Situ Ligation Protocols.” Angew. Chem., Int. Ed. 2023, 62, e202211794. DOI: 10.1002/anie.202211794 [html]
(40) Rein, J.; Lin, S.*; Kalyani, D.*; Lehnherr, D.* High-Throughput Experimentation for Electrochemistry. In The Power of High-Throughput Experimentation: General Topics and Enabling Technologies for Synthesis and Catalysis; Emmert, M. H., Jouffroy, M., Leitch, D. C., Eds; ACS Symposium Series, Vol. 1419; American Chemical Society, 2022; pp 167–187. DOI: 10.1021/bk-2022-1419.ch010 [html] Invited book chapter.
(39) Novaes, L. F. T.; Wang, Y.; Liu, J.; Riart-Ferrer, X.; Lee, W.-C. C.; Fu, N.; Ho, J. S. K.; Zhang, X. P.*; Lin, S.* “Electrochemical Diazidation of Alkenes Catalyzed by Manganese Porphyrin Complexes with Second-Sphere Hydrogen-Bond Donors.” ACS Catal. 2022, 12, 14106–14112. DOI: 10.1021/acscatal.2c05186 [html]
(38) Wu, X.; Gannett, C. N.; Liu, J.; Zeng, R.; Novaes, L. F. T.; Wang, H.; Abruña, H. D.*; Lin, S.* “Intercepting Hydrogen Evolution with Hydrogen-Atom Transfer: Electron-Initiated Hydrofunctionalization of Alkenes.” J. Am. Chem. Soc. 2022, 144, 17783–17791. DOI: 10.1021/jacs.2c08278 [html]
(37) Wu, X.; Chang, Y.; Lin, S.* “Titanium Radical Redox Catalysis Reactions, and Modes of Activation.” Chem 2022, 8, 1805–1821. DOI: 10.1016/j.chempr.2022.06.005 [html] Invited perspective. Dedicated to the occasion of Prof. John McMurry’s 80th birthday
(36) Guo, S.; Kim, M. J.; Siu, J. C.; von Windheim, N.; Gall, K.; Lin, S.; Wiley, B. J.* “Eight-Fold Intensification of Electrochemical Azidooxygenation with a Flow-Through Electrode.” ACS Sustainable Chemistry & Engineering 2022, 10, 7648–7657. DOI: 10.1021/acssuschemeng.2c01525 [html]
(35) Martinez Alvarado, J. I.; Meinhardt, J. M.; Lin, S.* “Working at the Interfaces of Data Science and Synthetic Electrochemistry.” Tetrahedron Chem 2022, 1, 100012. DOI: 10.1016/j.tchem.2022.100012 [html]
Invited contribution for the inaugural issue of Tetrahedron Chem
(34) Zhang, W.; Lu, L.; Zhang, W.; Wang, Y.; Ware, S.; Mondragon, J.; Rein, J.; Strotman, N.; Lehnherr, D.; See, K.*; Lin, S.* “Electrochemically Driven Cross-Electrophile Coupling of Alkyl Halides.” Nature 2022, 604, 292–297. DOI: 10.1038/s41586-022-04540-4 [html] [open-access]
(33) Novaes, L. F. T.; Ho, J. S. K.; Mao, K.; Liu, K.; Tanwar, M.; Neurock, M.; Villemure, E.; Terrett, J. A.*; Lin, S.* “Exploring Electrochemical C(sp3)–H Oxidation for the Late-Stage Methylation of Complex Molecules.” J. Am. Chem. Soc. 2022, 144, 1187–1197. DOI: 10.1021/jacs.1c09412 [html]
(32) Park, S. H.; Ju, M.; Ressler, A. J.; Shim, J.; Kim, H.*; Lin, S.* “Reductive Electrosynthesis: A New Dawn.” Aldrichimica Acta 2021, 54, 17–27. ISSN: 0002-5100 [html] Invited review.
(31) Wood, D. P.; Guan, W.; Lin, S.* “Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides.” Synthesis 2021, 53, 4213–4220. DOI: 10.1055/s-0037-1610779 [html]
Invited contribution for Sarah Reisman’s Margaret Faul Women in Chemistry Award
(30) Rein, J.; Annand, J. R.; Wismer, M. K.; Fu, J.; Siu, J. C.; Klapars, A; Strotman, N. A.; Kalyani, D.*; Lehnherr, D.*; Lin, S.* “Unlocking the Potential of High-Throughput Experimentation for Electrochemistry with a Standardized Microscale Reactor.” ACS Cent. Sci. 2021, 8, 1347–1355. DOI: 10.1021/acscentsci.1c00328 [html]
(29) Novaes, L. F. T.; Liu, J.; Shen, Y.; Lu, L.; Meinhardt, J. M.; Lin, S.* “Electrocatalysis as an Enabling Technology for Organic Synthesis.” Chem. Soc. Rev. 2021, 50, 7941–8002. DOI: 10.1039/D1CS00223F [html] Invited review.
(28) Nelson, H.*; Siu. J.C.; Saha, A.; Cascio, D.; Wu, S.-B.; Lu, C.; Rodriguez, J. A.; Houk, K. N.*; Lin, S.* “Isolation and X-ray Crystal Structure of an Electrogenerated TEMPO–N3 Charge-Transfer Complex.” Org. Lett. 2021, 23, 454–458. DOI: 10.1021/acs.orglett.0c03966 [html]
(27) Lu, L.; Siu, J. C.; Lai, Y.; Lin, S.* “An Electroreductive Approach to Radical Silylation via the Activation of Strong Si–Cl Bonds.” J. Am. Chem. Soc. 2020, 142, 21272–21278. DOI: 10.1021/jacs.0c10899 [html]
Highlighted on Organic Chemistry Portal Abstracts and in Org. Chem. Highlights
(26) Zhang, W.; Lin, S.* “Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.” J. Am. Chem. Soc. 2020, 142, 20661–20670. DOI: 10.1021/jacs.0c08532 [html]
Highlighted on Organic Chemistry Portal
(25) Robinson, S. G.; Wu, X.; Jiang, B.; Sigman, M. S.*; Lin, S.* “Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3+2] Cycloaddition.” J. Am. Chem. Soc. 2020, 142, 18471–18482. DOI: 10.1021/jacs.0c07128 [html]
Highlighted in Org. Chem. Highlights
(24) Liu, J.; Lu, L.; Wood, D.; Lin, S.* “New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry.” ACS Cent. Sci. 2020, 6, 1317–1340. DOI: 10.1021/acscentsci.0c00549 [html]
(23) Song, L.; Fu, N.; Ernst, B. G.; Lee, W. H.; Lin, S.* “Dual Electrocatalysis Enables Enantioselective Hydrocyanation of Conjugated Alkenes.” Nat. Chem. 2020, 12, 747–754. DOI: 10.1038/s41557-020-0469-5 [html] [open full-text access]
(22) Siu, J. C.; Fu, N.; Lin, S.* “Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.” Acc. Chem. Res. 2020, 53, 547–560. DOI: 10.1021/acs.accounts.9b00529 [html]
(21) Novaes, L. F. T.; Lin, S.* “Electrocatalytic Diazidation of Alkenes.” Trends in Chem. 2020, 2, 84–85. DOI: 10.1016/j.trechm.2019.10.005 [html]
(20) Zhang, W.; Carpenter, K.; Lin, S.* “Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols.” Angew. Chem., Int. Ed. 2020, 59, 409–417. DOI: 10.1002/ange.201910300 [html]
(19) Kim, H.; Kim, H.; Lambert, T.*; Lin, S.* “Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials.” J. Am. Chem. Soc. 2020, 142, 2087–2092. DOI: 10.1021/jacs.9b10678 [html] For the ChemRxiv preprint version, see [html]
(18) McCallum, T.; Wu, X.; Lin, S.* “Recent Advances in Titanium Radical Redox Catalysis.” J. Org. Chem. 2019, 84, 14369–14380. DOI: 10.1021/acs.joc.9b02465 [html]
(17) Fu, N.; Song, L.; Liu, J.; Shen, Y.; Siu, J. C.; Lin, S.* “New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.” J. Am. Chem. Soc. 2019, 141, 14480–14485. DOI: 10.1021/jacs.9b03296 [html]
(16) Lu, L.; Fu, N.; Lin, S.* “Three-Component Chlorophosphinoylation of Alkenes via Anodically Coupled Electrolysis.” Syn. Lett. 2019, 30, 1199–1203. DOI: 10.1055/s-0039-1689934 [html]
An invited contribution to the Cluster Electrochemical Synthesis and Catalysis
(15) Ye, K-Y.; McCallum, T.; Lin, S.* “Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols.” J. Am. Chem. Soc. 2019, 141, 9548–9554. DOI: 10.1021/jacs.9b04993 [html]
(14) Siu, J. C.; Parry, J. B.; Lin, S.* “Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.” J. Am. Chem. Soc. 2019, 141, 2825–2831. DOI: 10.1021/jacs.8b13192 [html]
(13) Fu, N.; Shen, Y.; Allen, A.R.; Song, L.; Ozaki, A.; Lin, S.* “Mn-catalyzed Electrochemical Chloroalkylation of Alkenes.” ACS Catal. 2019, 9, 746–754. DOI: 10.1021/acscatal.8b03209 [html]
(12) Wu, X.; Hao, W.; Ye, K-Y.; Jiang, B.; Pombar, G.; Song, Z.; Lin, S.* “Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors.” J. Am. Chem. Soc. 2018, 140, 14836–14843. DOI: 10.1021/jacs.8b08605 [html]
(11) Siu, J. C.; Sauer, G. S.; Saha, A.; Macey, R. L.; Fu, N.; Chauvirie, T.; Lancaster, K. M.*; Lin, S.* “Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO–N3Charge-Transfer Complex.” J. Am. Chem. Soc. 2018, 40, 12511–12520. DOI: 10.1021/jacs.8b06744 [html]
(10) Fu, N.; Sauer, G. S.; Lin, S.* “A general, electrocatalytic approach to the synthesis of vicinal diamines.” Nat. Protoc. 2018, 13, 1725–1743. DOI: 10.1038/s41596-018-0010-0 [PDF][HTML]
(9) Ye, K-Y.; Song, Z.; Sauer, G. S.; Harenberg, J. H.; Fu, N.; Lin, S.* “Synthesis of Chlorotrifluoromethylated Pyrrolidines by Electrocatalytic Radical Ene‐Yne Cyclization.” Chem. Eur. J. 2018, 24, 12274–12279. DOI:10.1002/chem.201802167 (Young Chemists Special Issue). [html]
(8) Sauer, G. S.; Lin, S.* “An Electrocatalytic Approach to the Radical Difunctionalization of Alkenes.” ACS Catal. 2018, 8, 5175–5187. DOI: 10.1021/acscatal.8b01069 (Invited Perspective). [html]
(7) Hao, W.; Harenberg, J. H.; Wu, X.; Macmillan, S. N.; Lin, S.* “Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay.” J. Am. Chem. Soc. 2018, 140, 3514–3517. DOI: 10.1021/jacs.7b13710 [html]
(6) Ye, K.; Pombar, G.; Fu, N.; Sauer, G. S.; Keresztes, I.; Lin, S.* “Anodically Coupled Electrolysis for the Heterodifunctionalization of Alkenes.” J. Am. Chem. Soc. 2018, 140, 2438–2441. DOI: 10.1021/jacs.7b13387 [html]
(5) Peterson, B. M.; Lin, S.*; Fors, B. P.* “Electrochemically Controlled Cationic Polymerization of Vinyl Ethers.” J. Am. Chem. Soc. 2018, 140, 2076–2079. DOI: 10.1021/jacs.8b00173 [html]
(4) Parry, J. B .; Fu, N.; Lin, S.* “Electrocatalytic Difunctionalization of Olefins as a General Approach to the Synthesis of Vicinal Diamines.” Synlett 2018, 29, 257–265. DOI: 10.1055/s-0036-1591749 (Invited Account). [html]
(3) Fu, N.; Sauer, G. S.; Lin, S.* “Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources.” J. Am. Chem. Soc. 2017, 139, 15548–15553. DOI: 10.1021/jacs.7b09388. [html]
(2) Hao, W.; Wu, X.; Sun, J. Z.; Siu, J. C.; MacMillan, S. N.; Lin, S.* “Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes.” J. Am. Chem. Soc. 2017, 139, 12141–12144. DOI: 10.1021/jacs.7b06723. [html]
Highlighted in SynForm
(1) Fu, N.; Sauer, G. S.; Saha, A.; Loo, A; Lin, S.* “Metal-catalyzed electrochemical diazidation of alkenes.” Science 2017, 357, 575–579. [Abstract][Full Text]
Highlighted in Chemical and Engineering News, Cornell Chronicle, and SynForm
Editorials and Commentaries:
(2) Ackermann, L.*; Lin, S.* “Special Collection on Organic Electrocatalysis.” Eur. J. Org. Chem. 2023, xxxxxx. [html]
(1) Minteer, S. D.*; Chen, J.*; Lin, S.*; Crudden, C.; Dehnen, S.; Kamat, P.; Kozlowski, M.; Masson, G.; Miller, S. J. “New Guidelines for Presenting Electrochemical Data in All ACS Journals.” Org. Lett. 2023, 25, 1999–2000. [html]
Patents:
(1) Lin, S.; Fu, N.; Sauer, G. S. “Electrocatalytic Alkene Diazidation”, US Patent 11,479,867.