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The Wang group will develop new catalysts, conditions, and reagents for organic synthesis. Investigations will focus on the development of methods for the activation and functionalization of unreactive but widely available carbon sources, as well as the stereoselective formation of weakly polarized carbon-carbon and carbon-heteroatom bonds under functional group tolerant and operationally simple catalytic conditions. Non-noble transition metal activation of hydrocarbons and ion pairing control of regio- and stereochemical outcome will be pursued as strategies for selective transformations of value to the synthesis of compounds of interest to the biomedical or materials sciences. Tools of physical organic chemistry and computational investigations will be applied to uncover mechanistic insights for rational optimization of chemical transformations.
- 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)
Awards
Recent Publications
“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
