Xin Cui

Image of Xin Cui

Xin Cui

Assistant Professor

B.S. University of Science and Technology of China (USTC), 2003
Ph.D. University of Science and Technology of China (USTC), 2008

Email

Hand Lab 3338

(662) 325-6805

CV

Research Interests

Research in our laboratory focuses on organic chemistry, catalysis, and medicinal chemistry. We are particularly interested in exploring new chemical processes that utilize earth-abundant and biocompatible catalysts to construct value-added molecules in a rapid and selective manner.

Catalytic processes for rapid formation of multiple chemical bonds

Our research efforts are devoted to the revealing of new catalytic reactivity that involves one-step selective formation of multiple carbon-carbon and carbon-heteroatom bonds. Such reactivity would allow for effective construction of complex skeletons and polyfunctionalized molecules. Specifically, we are interested in new multicomponent cyclization systems that utilize simple and noncyclic starting materials for constructing heterocyclic and heteropolycyclic structures. Mechanistic study-guided catalyst design is used as a powerful tool to investigate new pathways for solving some of the long standing problems.

Selective functionalization of unsaturated hydrocarbons

Further development of new transformations of unsaturated hydrocarbons will always bring exciting opportunities for synthetic chemistry and other applicable areas such as fine chemical, pharmaceutical, and material sciences. In our lab, we are exploring new types of catalytic activation of heterocyclic small rings for selective functionalization of unactivated alkenes and related unsaturated hydrocarbons. Through the development of both transition and main group element-based catalysts, together with ligand design, these catalytic systems are expected to be able to effectively control and switch chemoselectivity and stereoselectivity. The catalytic processes developed in our group are applied for the syntheses of synthetically and pharmaceutically important molecules, agrochemicals, and functional materials. 

Postions Open

Research positions in our group are available to both graduate and undergraduate students.  Enthusiastic and motivated students who are interested in synthetic chemistry and catalysis are encouraged to contact Dr. Cui for further details.

References

Selected Journal Publications

25. Zhou, H.; Chaminda Lakmal, H. H.; Baine, M. J.; Valle, U. H.; Xu, X.; Cui, X.* “Catalytic [2 + 2 + 2] cycloaddition with indium(III)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes” Chem. Sci. 2017, 8, 6520. [link]

24. Xu, X.; Wang, Y.; Cui, X.; Wojtas, L.; Zhang, X. P. “Metalloradical Activation of α-Formyldiazoacetates for Catalytic Asymmetric Radical Cyclopropanation of Alkenes” Chem. Sci. 2017, 8, 4347.

23. Wang, Y.; Wen, X.; Cui, X.; Wojtas, L.; Zhang, X. P. “Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis” J. Am. Chem. Soc. 2017, 139, 1049.

22. 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.

21. Goswami, M.; Lyaskovskyy, V.; Domingos, S.; Buma, W. J.; Woutersen, S.; Troeppner, O.; Ivanović-Burmazović, I.; Lu, H.; Cui, X.; Zhang, X. P.; Reijerse, E.; DeBeer, S.; van Schooneveld, 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.

20. Subbarayan V; Jin, L. M.; Cui, X.; Zhang, X. P. “Room temperature activation of aryloxysulfonyl azides by [Co(II)(TPP)] for selective radical aziridination of alkenes via metalloradical catalysis”, Tetrahedron Lett. 2015, 56, 3431.

19. 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.

18.  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(sp(2))-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.

17.  Ruppel, J. V.; Cui, X.; Xu, X.; Zhang, X. P. “Stereoselective Intramolecular Cyclopropanation of α-Diazoacetates via Co(II)-Based Metalloradical Catalysis” Org. Chem. Front. 2014, 1, 515.

16.  Xu X., Zhu, S.-F.; Cui, X.; Wojtas, L.; Zhang, X. P. “Cobalt(II)-Catalyzed Asymmetric Olefin Cyclopropanation with α-Ketodiazoacetates”, Angew. Chem. Int. Ed. 2013, 52, 11857.

15.  Jin, L.-M.; Xu, X.; Lu, H.; Cui, X.; Wojtas, L.; Zhang, X. P. “Effective Synthesis of Chiral N-Fluoroaryl Aziridines through Enantioselective Aziridination of Alkenes with Fluoroaryl Azides”, Angew. Chem. Int. Ed. 2013, 52, 5309.

14.  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.

 

13.  Zhu, S.-F.; Cui, X.; Zhang, X. P. “Ligand Effect on Cobalt(II)-Catalyzed Asymmetric Cyclopropanation with Diazosulfones-Approaching High Stereoselectivity through Modular Design of D2-Symmetric Chiral Porphyrins”, Eur. J. Inorg. Chem. 2012, 430.

12.  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.

11.  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.

10.  Cui, X.; Zhang, X. P. “Iron(III) meso-Tetraphenylporphine Chloride” e-EROS Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2011, DOI: 10.1002/047084289X.rn01388.

9.   Cui, X.; Li, J.; Fu, Y.; Liu, L.; Guo, Q.-X. “Regioselective Pd-Catalyzed Indolization of 2-Bromoanilines with Internal Alkynes using Phosphine-free Ligands”, Tetrahedron Lett. 2008, 49, 3458.

8.   Cui, X.; Li, J.; Zhang, Z.-P.; Fu, Y.; Liu, L.; Guo, Q.-X. “Pd(quinoline-8-carboxylate)2 as a Low-priced, Phosphine-free Catalyst for Heck and Suzuki Reactions”, J. Org. Chem. 2007, 72, 9342.

7.   Cui, X.; Zhou, Y.; Wang, N.; Liu, L.; Guo, Q.-X. “N-Phenylurea as an inexpensive and efficient ligand for Pd-catalyzed Heck and room-temperature Suzuki reactions”, Tetrahedron Lett. 2007, 48, 163.

6.   Cui, X.; Qin, T.; Wang, J.-R.; Liu, L.; Guo, Q.-X. “Pd(N,N-dimethyl-b-alaninate)2 as a high-turnover-number, phosphine-free catalyst for the Suzuki reaction”, Synthesis, 2007, 3, 393.

5.    Cui, X.; Li, J.; Liu, L.; Guo, Q.-X. “1,3-Dicarbonyl compounds as phosphine-free ligands for Pd-catalyzed Heck and Suzuki reactions”, Chin. Chem. Lett. 2007, 18, 625.

4.     Tao, C.-Z.; Li, J.; Cui, X.; Fu, Y.; Liu, L.; Guo, Q.-X. “Cu-catalyzed cross-couplings under ligandless conditions”, Chin. Chem. Lett. 2007, 18, 1199.

3.    Tao, C.-Z.; Cui, X.; Li, J.; Liu, A.-X., Liu, L.; Guo, Q.-X. “Copper-catalyzed synthesis of aryl azides and 1-aryl-1,2,3-triazoles from boronic acids”, Tetrahedron Lett. 2007, 48, 3525.

2.   Wang, J.-R.; Fu, Y.; Zhang, B.-B.; Cui, X.; Liu, L.; Guo, Q.-X. “Palladium-Catalyzed Aerobic Oxidation of Amines”, Tetrahedron Lett. 2006, 47, 8293.

1.   Cui, X.; Li, Z.; Tao, C.-Z.; Xu, Y.; Li, J.; Liu, L.; Guo, Q.-X. “N,N-Dimethyl-b-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction”, Org. Lett. 2006, 8, 2467.

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Book Chapters:

1.    Cui, X.; Zhang, X. P. “C–C Bond Formation Using Carbenes” In Science of Synthesis: Catalytic Transformations via C–H Activation series; eds. Yu, J. -Q.; Thieme, 2016, Vol. 2, pp. 63–94.

2.    Cui, X.; Zhang, X. P. “Asymmetric C–H Functionalization by Transition Metal-Catalyzed Carbene Transfer Reactions” In Comprehensive Organic Synthesis 2nd Edition; eds. Knochel, P.; Molander, G. A.; Amsterdam: Elsevier, 2014, Vol. 7, pp. 86–120.

3.  Cui, X.; Zhang, X. P. “Cobalt-Mediated Carbene Transfer Reactions” In Contemporary Carbene Chemistry; eds. Moss, R. A.; Doyle, M. P.; John Wiley & Sons, 2013, Chapter 15. pp. 491-525.

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