Yiming Wang | Department of Chemistry

The Wang Lab is currently accepting new graduate students. Apply here.

The Wang Group is engaged in the discovery and development of new catalytic reactions for efficient, sustainable organic synthesis. Research activities in the group focus on the development of novel catalysts, reagents, and conditions for the construction of challenging bonds and stereocenters found in products of interest to pharmaceutical and materials research.

These efforts have included the development of a new mode of catalytic C–H functionalization that leverages the enhanced acidity of molecules containing C–C multiple bonds upon π-coordination to cationic metal centers. The acidity enhancement allows for deprotonation and subsequent functionalization under mild conditions, enabling the redox-neutral and selective functionalization of substrates ranging from simple hydrocarbons (pK_a 30 to 45) to derivatives of pharmaceutically active compounds:

Awards

National Institutes of Health Ruth L. Kirschstein NRSA Individual Postdoctoral Fellowship (2014-2017)
Outstanding Graduate Student Instructor Award, UC Berkeley (2011)
Phi Beta Kappa, Harvard College (2008)

Recent Publications

"Chirality Matching Induces Molecularity Change and Diastereodivergence in Iridium-Catalyzed Allylation of Propargylic C−H Bonds" Ding, R.; Xie, P.-P.; Zhu, J.; Wang, Y.-M.*; Liu, P.* ACS Catal., 2026, 16, 8846-8857.

"Intramolecular asymmetric propargylation of esters and imides: C–H functionalisation enables stereocontrolled access to UCS1025A" Corcoran, J. C.; Zhu, J.; Semenick, M. A.; Welser, A. L.; Wang, Y.-M.* Chem. Sci., 2025, 16, 12879-12884.

"Asymmetric Synthesis of Propargylic and Allenic Silanes, Germanes, and Stannanes" Chang, H.‡; Wang, R.‡; Wang, Y.-M.* Chem. Asian J., 2025, 20, e00105.

"Access to fluorinated dienes through hydrofluorination of 2-En-4-ynoates" Xia, Y.‡; Charlack, A. D.‡; Guo, R.; Wade, N. W.; Wang, Y.-M.* Org. Chem. Front., 2025, 12, 1425.

"An Umpolung Approach for Iron-Mediated Propargylic C–H Etherification" Xia, Y.; Zhu, J.; Durham, A. C.; Wang, Y.-M.* Angew. Chem. Int. Ed. 2024, 63, e202413017.

"Iridium-Catalyzed Propargylic C–H Trifluoromethylthiolation and Related Processes" Yu, J.; Xia, Y.; Dey, S.; Zhu, J.; Cheung, K. S.; Geib, S. J.; Wang, Y.-M.* J. Am. Chem. Soc. 2024, 146, 27998. (Correction: doi: 10.1021/jacs.4c13920)

"Transition Metal Mimetic π-Activation by Cationic Bismuth(III) Catalysts for Allylic C–H Functionalization of Olefins Using C═O and C═N Electrophiles" Wang, R.; Martínez, S.; Schwarzmann, J.; Zhao, C. Z.; Ramler, J.; Lichtenberg, C.*; Wang, Y.-M.* J. Am. Chem. Soc. 2024, 146, 22122.

“Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C–H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation,” Dey, S.; Charlack, A. D.; Durham, A. C.; Zhu, J.; Wang, Y.; Wang, Y.-M.* Org. Lett. 2024, 26, 3355-3360

“A C–H functionalization approach to diverse nitrogenous scaffolds through conjugate addition of catalytic allyliron nucleophiles,” Scrivener, S. G.; Wang, Y.-M.* Chem. Sci. 2024, 15, 8850-8857

“Enantioselective and Regiodivergent Synthesis of Propargyl- and Allenylsilanes through Catalytic Propargylic C−H Deprotonation,” Zhu, J.; Xiang, H.; Chang, H.; Corcoran, J. C.; Ding, R.; Xia, Y.; Liu, P.; Wang, Y-M.* Angew. Chem. Int. Ed. 2024, 63, e202318040

“Iron-Mediated C−H Functionalization of Unactivated Alkynes for the Synthesis of Derivatized Dihydropyrrolones: Regioselectivity Under Thermodynamic Control,” Durham, A.C.; Liu, C.R.; Wang, Y.-M. Chem. Eur. J. 2023, 29, e202301195

“Iron-Catalyzed Coupling of Alkenes and Enones: Sakurai–Michael-type Conjugate Addition of Catalytic Allyliron Nucleophiles,” Scrivener, S.G.; Wang, Y.; Wang, Y.-M.* Org. Lett. 2023, 25, 1420-1424

“Designed Iron Catalysts for Allylic C−H Functionalization of Propylene and Simple Olefins,” Wang, R.; Wang, Y.; Ding, R.; Staub, P.B.; Zhao, C.Z.; Liu, P.; Wang, Y.-M. Angew. Chem. Int. Ed. 2023, 62, e202216309

“Synthesis of 1,1-Disubstituted Allenylic Silyl Ethers through Iron-Catalyzed Regioselective C(sp2)–H Functionalization of Allenes,” Ding, R.; Wang, Y.; Wang, Y.-M.* Synthesis 2023, 55, 733-743

“Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents,” Corcoran, J.C.; Guo, R.; Xia, Y.; Wang, Y.-M.* Chem. Commun. 2022, 58, 11523-11526

“α-C-H Functionalization of π-Bonds Using Iron Complexes,” Xia, Y.; Wang, Y.-M. Handbook of CH-Functionalization 2022

“Enantioselective and Diastereodivergent Allylation of Propargylic C–H Bonds,” Zhu, J.; Wang, Y.; Charlack, A.D.; Wang, Y.-M.* J. Am. Chem. Soc. 2022, 144, 15480-15487

“Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)–H functionalisation,” Xia, Y.; Wade, N.W.; Palermo, P.N.; Wang, Y*.; Wang, Y.-M.* Chem. Commun. 2021, 57, 13329-13332

“Regiocontrolled Coupling of Alkynes and Dipolar Reagents: Iron-Mediated [3 + 2] Cycloadditions Revisited,” Zhu, J.; Durham, A.C.; Wang, Y.; Corcoran, J.C.; Zuo, X.-D.; Geib, S.J.; Wang, Y.-M.* Organometallics 2021, 40, 2295-2304

“Iron-catalyzed α-C–H functionalization of π-bonds: cross-dehydrogenative coupling and mechanistic insights,” Wang, Y.; Zhu, J.; Guo, R.; Lindberg, H.; Wang, Y.-M.* Chem. Sci. 2020, 11, 12316-12322

“Redox-Neutral Propargylic C-H Functionalization by Using Iron Catalysis,” Durham, A.C.; Wang, Y.; Wang, Y.-M.* Synlett 2020, 31, 1747

“Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroboratesas Tunable Reagents,” Guo, R.; Qi, X.; Xiang, H.; Geaneotes, P.; Wang, R.; Liu, P.; Wang, Y-M Angew. Chem. Int. Ed. 2020, 59, 16249-16800

“Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)–H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes,” Wang, Y.; Scrivener, S.G.; Zuo, X.-D.; Wang, R.; Palermo, P.N.; Murphy, E.; Durham, A.C.; Wang, Y.-M.* J. Am. Chem. Soc. 2021, 143, 14998-15004

“α-C–H Functionalization of π-Bonds Using Iron Complexes: Catalytic Hydroxyalkylation of Alkynes and Alkenes,” Wang, Y.; Zhu, J; Durham, A.C.; Lindberg, H.; Wang, Y-M* J. Am. Chem. Soc. 2019, 141, 19594-19599

“Remote Migratory Cross-Electrophile Coupling and Olefin Hydroarylation Reactions Enabled by in Situ Generation of NiH,” Chen, F.; Chen, K.; Zhang, Y.; He, Y.; Wang, Y-M.*; Zhu, S.* J. Am. Chem. Soc. 2017, 139, 13929-13935

“Enantioselective CuH-Catalyzed Hydroallylation of Vinylarenes,” Wang, Y.-M.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 5024

“Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach,” Wang, Y.-M.; Bruno, N. C.; Placeres, Á. L.; Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 10524-10527

“An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols,” Zi, W.(+); Wang, Y.-M.(+); Toste, F. D. (+): Equally contributing authors. J. Am. Chem. Soc. 2014, 136, 12864-12867

“Enantioselective Halocyclization using Reagents Tailored for Chiral Anion Phase-Transfer Catalysis,” Wang, Y.-M.; Wu, J.; Hoong, C.; Rauniyar, V.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 12928-12931

“Chiral (Acyclic Diaminocarbene)Gold(I)-Catalyzed Dynamic Kinetic Asymmetric Transformation of Propargyl Esters,” Wang, Y.-M.; Kuzniewski, C. N.; Rauniyar, V.; Hoong, C.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 12972-12975