Song Lin

Overview

The research in the Lin Lab lies in the broadly defined area of organic chemistry, with specific interests in electrosynthesis, asymmetric catalysis and organic materials.

Research Focus

We will use our expertise in organic chemistry and electrochemistry to develop new catalytic methods to address unsolved problems in organic and materials synthesis. Particular emphases will be placed on the rational design of catalysts and the creative use of electrochemistry that will allow for the facile and selective conversion of readily available starting materials, such as sugars, CO2 and abundant natural products, into highly functionalized and value-added products, such as pharmaceuticals and polymers.

Publications

• 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.
• 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.
• 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.
• Nelson, H. M.; Siu, J. C.; Saha, A.; Cascio, D.; MacMillan, S. N.; Wu, S.-B.; Lu, C.; Rodríguez, 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.
• 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.
• 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.
• 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.
• Liu, J.; Lu, L.; Wood, D. P.; Lin, S. “New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry.” ACS Cent. Sci. 2020, 6, 1317–1340.
• Song, L.; Fu, N.; Ernst, B. G.; Lee, W. H.; Frederick, M. O.; DiStasio, R. A. Jr.; Lin, S. “Dual Electrocatalysis Enables Enantioselective Hydrocyanation of Conjugated Alkenes.” Nat. Chem. 2020, 12, 747–754.
• 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, 142, 2087-2092.
• Zhang, W.; Carpenter, K.; Lin, S. “Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols.” Angew. Chem., Int. Ed. 2019, 141, 14480-14485.
• 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.
• 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.
• 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.
• 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.
• Siu, J. C.; Sauer, G. S.; Saha, A.; Macey, R. L.; Fu, N.; Chauvirie, T.; Lancaster, K. L.; Lin, S. “Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO–N3 Charge-Transfer Complex.” J. Am. Chem. Soc. 2018, 40, 12511-12520.
• Fu, N.; Sauer, G. S.; Lin, S. “A general, electrocatalytic approach to the synthesis of vicinal diamines.” Nat. Protoc. 2018, 13, 1725–1743.
• Sauer, G. S.; Lin, S. “An Electrocatalytic Approach to the Radical Difunctionalization of Alkenes.” ACS Catal. 2018, 8, 5175–5187.
• 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.
• 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.
• Peterson, B. M.; Lin, S.; Fors, B.P.  “Electrochemically Controlled Cationic Polymerization of Vinyl Ethers” J. Am. Chem. Soc. 2018, 140, 2076–2079.
• Fu, N.; Sauer, G. S.; Lin, S. “Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources.” J. Am. Chem. Soc. 2017, 139, 15548–15553.
• 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.
• Fu, N.; Sauer, G. S.; Saha, A.; Loo, A; Lin, S. “Metal-catalyzed electrochemical diazidation of alkenes”, Science 2017, 357, 575–579.
• Kennedy, C. R.;* Lin, S.;* Jacobsen, E. N. “The cation–π interactions in small-molecule catalysis”, Angew. Chem., Int. Ed. 2016, 55, 12596–12624. (* co-first author)
• Cao, Z.; Kim, D.; Yu, Y.; Xu, J.; Lin, S.; Wen, X.; Nichols, E. M.; Jeong, K.; Reimer, J. A.; Yang, P.; Chang, C. J. “A molecular surface functionalization approach to tuning nanoparticle electrocatalysts for carbon dioxide reduction”, J. Am. Chem. Soc. 2016, 138, 8120–8125.
• Lin, S.;* Diercks, C. S.;* Zhang, Y.-B.;* Kornienko, N.; Nichols, E. M.; Zhao, Y.; Paris, A. R.; Kim, D.; Yang, P.; Yaghi, O. M.; Chang, C. J. “Covalent organic frameworks comprising cobalt porphyrins for catalytic CO2 reduction in water”, Science 2015, 349, 1208–1213. (* co-first author)
• Kornienko, N.; Zhao, Y.; Kley, C.; Zhu, C.; Kim, D.; Lin, S.; Chang, C. J.; Yaghi, O. M.; Yang, P. “Metal-organic frameworks for electrocatalytic reduction of carbon dioxide”, J. Am. Chem. Soc. 2015, 137, 14129–14135.
• Rogers, C.; Chen, C.; Pedramrazi, Z.; Omrani, A. A.; Tsai, H.-Z.; Jung, H. S.; Lin, S.; Crommie, M. F.; Fischer, F. R. “Closing the nanographene gap: surface-assisted synthesis of peripentacene from 6,6’-bipentacene precursors”, Angew. Chem., Int. Ed. 2015, 54, 15143–15146.
• Zhang, H.; Lin, S.; Jacobsen, E. N. “Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts”, J. Am. Chem. Soc. 2014, 136, 16485–16488.
• Lin, S.; Jacobsen, E. N. “Thiourea-catalysed ring opening of episulfonium ions with indole derivatives by means of stabilizing non-covalent interactions”, Nature Chem. 2012, 4, 817–824.
• Knowles, R. R.; Lin, S.; Jacobsen, E. N. “Enantioselective thiourea-catalyzed polycyclizations”, J. Am. Chem. Soc. 2010, 132, 5030–5032.
• Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. “Cross dehydrogenative arylation (CDA) of a benzylic C–H bond with arenes by iron catalysis”, Angew. Chem., Int. Ed. 2009, 48, 3817–3820. 
• Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.H.; Shi, Z.-J. “Intra/Intermolecular direct allylic alkylation via Pd(II)-catalyzed allylic C–H activation”, J. Am. Chem. Soc. 2008, 130, 12901–12903.

In the news

• Two chemistry professors win Cope Scholar Award
• Bulky size frustrates radical molecules to boost chemical reactions
• A&S honors 23 faculty with endowed professorships
• Electrochemistry converts carbon to useful molecules
• Song Lin wins EPA Green Chemistry Challenge award
• Arts and Sciences faculty honored for teaching, advising excellence
• Chemist Song Lin honored by Chemical & Engineering News
• Electrosynthesis energizes sustainable drug development
• Three A&S professors honored with national chemistry awards
• $2M in New Frontier Grants boost high-impact A&S research
• Electrochemical reaction powers new drug discoveries
• Electric-Powered Organic Chemistry
• Chemistry professor receives young investigator award from Navy
• Twelve assistant professors win NSF early-career awards
• Chemists use electricity to amp up drug manufacturing

CHEM Courses - Fall 2024

• CHEM 4610 : Introduction to Organic Chemistry Research

CHEM Courses - Spring 2025

• CHEM 4610 : Introduction to Organic Chemistry Research
• CHEM 6650 : Advanced Organic Chemistry