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Peter  Zhang

Peter Zhang

Peter Zhang
Courtesy Professor





Ph.D., University of Pennsylvania
Postdoctoral Fellow, Massachusetts Institute of Technology


Metalloradical Catalysis (MRC) for Homolytic Radical Chemistry


One of the major efforts of our research program has centered on the development of fundamentally new catalytic systems for stereoselective chemical transformations and their applications for practical synthesis of organic molecules with biological and pharmaceutical interests. We are particularly interested in developing one-electron catalytic approaches for homolytic radical chemistry to harness the vast potential of radical reactions for stereoselective construction of molecular structures. To this end, we have formulated “Metalloradical Catalysis” (MRC) as a concept to guide the development of general approaches for controlling reactivity and selectivity of various radical processes. For achieving enantioselective radical reactions, we have developed a family of unique chiral metalloradical catalysts based on structurally well-defined Co(II) complexes of D2-symmetric chiral porphyrins with tunable electronic, steric, and chiral environments. These Co(II)-based metalloradical catalysts have shown to be highly effective for a wide range of stereoselective organic reactions, including alkene cyclopropanation, alkene aziridination, C–H alkylation, C–H amination and others. Due to their distinctive radical mechanisms that involve unprecedented metal-stabilized radical intermediates, such as α-metalloalkyl radicals (also known as metallocarbene radicals) and α-metalloaminyl radicals (also known as metallonitrene radicals), the Co(II)-based metalloradical systems enable addressing some long-standing challenges in these important organic transformations.

Current Funding

View our currently funded projects here.

Research Assistant Professor

Dr. Xin Cui

Postdoctoral Associates

Dr. Limei Jin, Dr. Kai Lang, Dr. Peng Sang, Dr. Xichen Xu and Dr. Xue Xu

Undergraduate Students

Cameron Felski, Nelson Garcia-Vasquez, McKenzie Marshall, Md Jamilur Rahman and Heather Vermilyear

Medical Students

Jennifer Lei

Graduate Students

Qigan Cheng

Recent Publications

  • Goswami, M.; Lyaskovskyy, V.; Domingos, S. R.; Buma, W. J.; Woutersen, S.; Troeppner, O.; Ivanovic-Burmazovic, I.; Lu, H.-J.; Cui, X.; Zhang, X. P.; Reijerse, E. J.; DeBeer S.; van Schooneveld, M. M.; Pfaff, F.; Ray, K.; de Bruin, B. “Characterization of Porphyrin-Co(III)-‘Nitrene Radical’ Species Relevant in Catalytic Nitrene Transfer Reactions” J. Am. Chem. Soc. 2015, 137, 5468–5479. [Link]
  • Cui, X.; Xu, X.; Jin, L.-M.; Wojtas, L.; Zhang, X. P. “Stereoselective Radical C–H Alkylation with Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis” Chem. Sci. 2015, 6, 1219–1224. [Link]
  • Lu, H.-J.; Li, C.-Q.; Jiang, H.-L.; Lizardi, C. L.; Zhang, X. P. “Chemoselective Amination of Propargylic C(sp3)-H Bonds via Co(II)-Based Metalloradical Catalysis” Angew. Chem. Int. Ed. 2014. [Link]
  • Paul, N. D.; Mandal, S.; Otte, M.; Cui, X.; Zhang, X. P.; de Bruin, B. “A Metalloradical Approach to 2H-Chromenes” J. Am. Chem. Soc. 2014, 136, 1090–1096. [Link]
  • Jin, L.-M.; Lu, H.-J.; Cui, Y.; Lizardi, C. L.; Arzua, T. N.; Wojtas, L.; Cui, X.; Zhang, X. P. “Selective Radical Amination of Aldehydic C(sp2)-H Bonds with Fluoroaryl Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions” Chem. Sci. 2014, 5, 2422–2427. [Link]
  • Xu, X.; Zhu, S.-F.; Cui, X.; Wojtas, L.; Zhang, X. P. “Cobalt(II)-Catalyzed Asymmetric Olefin Cyclopropanation with α-Ketodiazoacetates and Iodide-Promoted Stereospecific Epimerization of Resulting (E)-1,1-Cyclopropaneketoesters” Angew. Chem. Int. Ed. 2013, 52, 11857–11861. [Link]
  • Jin, L.-M.; Xu, X.; Lu, H.; Cui, X.; Wojtas, L.; Zhang, X. P. “Effective Synthesis of Chiral N-Fluoroaryl Aziridines via Enantioselective Aziridination of Alkenes with Fluoroaryl Azides” Angew. Chem. Int. Ed. 2013, 52, 5309–5313. [Link]
  • Cui, X.; Xu, X.; Wojtas, L.; Kim, M. M.; Zhang, X. P. “Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans” J. Am. Chem. Soc. 2012, 134, 19981–19984. [Link]
  • Meng, L.; Cheng, Q.; Kim, C.-S.; Gao, W.-Y.; Wojtas, L.; Chen, Y.-S.; Zaworotko, M. J.; Zhang, X. P.; Ma, S.-Q. “Crystal Engineering of a Microporous, Catalytically Active fcu Topology MOF Using a Custom-Designed Metalloporphyrin Linker” Angew. Chem. Int. Ed. 2012,51, 10082–10085. [Link]
  • Xu, X.; Lu, H.-J.; Ruppel, J. V.; Cui, X.; de Mesa, S. L.; Wojtas, L.; Zhang, X. P. “Highly Asymmetric Intramolecular Cyclopropanation of Acceptor-Substituted Diazoacetates by Co(II)-Based Metalloradical Catalysis: Iterative Approach for Development of New Generation Catalysts” J. Am. Chem. Soc. 2011, 133, 15292-15295. [Link]
  • Lyaskovskyy, V.; Suarez, A. I. O.; Lu, H.-J.; Zhang, X. P.; de Bruin, B. “Mechanism of Cobalt(II) Porphyrin-Catalyzed C–H Amination with Organic Azides: Radical Nature and H-Atom Abstraction Ability of Cobalt(III)-Nitrene Key Intermediates” J. Am. Chem. Soc. 2011, 133, 12264-12273. [Link]
  • Lu, H.-J.; Dzik, W. I.; Xu, X.; Wojtas, L.; de Bruin, B.; Zhang, X. P. “Experimental Evidence for Cobalt(III)-Carbene Radicals: Key Intermediates in Cobalt(II)-Based Metalloradical Cyclopropanation” J. Am. Chem. Soc. 2011, 133, 8518-8521. [Link]
  • Cui, X.; Xu, X.; Lu, H.-J.; Zhu, S.-F.; Wojtas, L.; Zhang, X. P. "Enantioselective Cyclopropenation of Alkynes with Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis" J. Am. Chem. Soc. 2011, 133, 3304-3307. [Link]
  • Wang, X.-S.; Meng, L.; Cheng, Q.-G.; Kim, C.-S.; Wojtas, L.; Chrzanowski, M.; Chen, Y.-S.; Zhang, X. P.; Ma, S.-Q. "A Three-Dimensional Porous Metal-Metalloporphyrin Framework Consisting of Nanoscopic Polyhedral Cages with a High Density of Open Metal Sites" J. Am. Chem. Soc. 2011, 133, 16322-16325. [Link]
  • Lu, H.-J.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. "Selective Intramolecular C–H Amination via Metalloradical Activation of Azides: Synthesis of 1,3-Diamines under Neutral and Nonoxidative Conditions" Angew. Chem. Int. Ed. 2010, 49, 10192–10196. [Link]
  • Zhu, S.-F.; Xu, X.; Perman, J. A.; Zhang, X. P. "A General and Efficient Cobalt(II)-Based Catalytic System for Highly Stereoselective Cyclopropanation of Alkenes with α-Cyano-Diazoacetates" J. Am. Chem. Soc. 2010, 132, 12796–12799. [Link]
  • Dzik, W. I.; Xu, X.; Zhang, X. P.; Reek, J. N. H.; de Bruin, B. "Carbene Radicals' in CoII(por)-Catalyzed Olefin Cyclopropanation" J. Am. Chem. Soc. 2010, 132, 10891–10902. [Link]