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Teaching Staff

Dr. HE, Jian

Dr. HE, Jian

Department of Chemistry, Faculty of Science, HKU

B.Sc. (Zhejiang University); Ph.D. (Scripps Research)


  • 3910 2193
  • Room 103, Hui Oi Chow Science Building, The University of Hong Kong, Pokfulam Road, Hong Kong

Research Overview:

 

The development of heterogeneous catalysts with high activity, selectivity, and stability is essential for rendering catalytic organic reactions practically useful, since they provide highly recyclable, scalable, and efficient setups in many large-scale chemical processes. Additionally, these catalysts may be utilized in continuous flow systems, which facilitates facile automation and improves product quality through easy separation. While numerous organic transformations have been achieved in homogeneous catalytic systems, the needs for addressing their synthetic limitations, such as high catalyst loadings, poor selectivity, and employment of toxic and expensive reagents, represent challenges and opportunities for the coming generation of chemists. Designing novel catalysts that marry the benefits of heterogeneous catalysis with those of homogeneous catalysis to solve the long-standing problems in organic synthesis is compelling and highly desirable. 

 

Direction 1

We design highly tunable solid matrices that can facilitate effective electron transfer and/or radical trapping processes, providing opportunities to further increase the catalytic reactivity compared with their homogeneous counterparts.

 

Direction 2

We synthesize functionalized polymers for heterogeneous catalysis. The synergistic effect of the dual-ligand systems may help promote the organic reactions which are difficult to realize in homogeneous transition-metal catalysis.

 

Direction 3

We collaborate with other synthetic biology labs to develop highly selective coupling reactions using artificial metalloenzymes.

 

Selected Publications

 

25. He, J.; Chen, C.; Fu, G. C.; Peters, J. C. Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers. ACS Catal. 20188, 11741-11748.

24. Shao, Q.; Wu, Q.; He, J.; Yu, J.-Q. Enantioselective γ-C(sp3)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis. J. Am. Chem. Soc. 2018140, 5322-5325.

23.  He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Palladium-Catalyzed Transformations of Alkyl C-H Bonds. Chem. Rev. 2017117, 8754-8786.

22. Shao, Q.; He, J.; Wu, Q.; Yu, J.-Q. Ligand-Enabled γ-C(sp3)-H Cross-Coupling of Nosyl-Protected Amines with Aryl- and Alkylboron Reagents. ACS Catal. 20177, 7777-7782.

21. Wang, H.-W.; Lu, Y.; Zhang, B.; He, J.; Xu, H.-J.; Kang, Y.-S.; Sun, W.-Y.; Yu, J.-Q. Ligand-Promoted Rhodium(III)-Catalyzed ortho-C-H Amination of Benzamides with Free Amines. Angew. Chem. Int. Ed. 201756, 7449-7453.

20. Pei, Q.-L.; Che, G.-D.; Zhu, R.-Y.; He, J.; Yu, J.-Q. An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary. Org. Lett. 201719, 5860-5863.

19. Zhu, R.-Y.; Saint-Denis, T. G.; Shao, Y.; He, J.; Sieber, J. D.; Senanayake, C. H.; Yu, J.-Q. Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds. J. Am. Chem. Soc. 2017139, 5724-5727.

18. He, J.; Shao, Q.; Wu, Q.; Yu, J.-Q. Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation. J. Am. Chem. Soc. 2017139, 3344-3347.

17. Fu, H.; Shen, P.-X.; He, J.; Zhang, F.; Li, S.; Wang, P.; Liu, T.; Yu, J.-Q. Ligand-Enabled Alkynylation of C(sp3)-H Bonds with Pd(II) Catalysts. Angew. Chem. Int. Ed. 201756, 1873-1876.

16. Wu, Q.-F.; Shen, P.-X.; He, J.; Wang, X.-B.; Zhang, F.; Shao, Q.; Zhu, R.-Y.; Mapelli, C.; Qiao, J. X.; Poss, M. A.; Yu, J.-Q. Formation of α-Chiral Centers by Asymmetric β-C(sp3)-H Arylation, Alkenylation, and Alkynylation. Science 2017355, 499-503.

15. Wang, P.; Li, G.-C.; Jain, P.; Farmer, M.; He, J.; Shen, P.-X.; Yu, J.-Q. Ligand-Promoted Meta-C-H Amination and Alkynylation. J. Am. Chem. Soc. 2016138, 14092-14099.

14. Lee, L.-C.; He, J.; Yu, J.-Q.; Jones, C. W. Functionalized Polymer-Supported Pyridine Ligands for Palladium-Catalyzed C(sp3)-H Arylation. ACS Catal. 20166, 5245-5250.

13. Jiang, H.;† He, J.;† Liu, T.; Yu, J.-Q. Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines. J. Am. Chem. Soc. 2016138, 2055-2059.

12. He, J.; Jiang, H.; Takise, R.; Zhu, R.-Y.; Chen, G.; Dai, H.-X.; Dhar, T. G. M.; Shi, J.; Zhang, H.; Cheng, P. T. W.; Yu, J.-Q. Ligand-Promoted Borylation of C(sp3)?H Bonds with Pd(II) Catalysts. Angew. Chem. Int. Ed. 201655, 785-789.

11. Zhu, R.-Y.; Tanaka, K.; Li, G.-C.; He, J.; Fu, H.-Y.; Li, S.-H.; Yu, J.-Q. Ligand-Enabled Stereoselective β-C(sp3)-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-Amino Acids. J. Am. Chem. Soc. 2015137, 7067-7070.

10. He, J.; Takise, R.; Fu, H.; Yu, J.-Q. Ligand-Enabled Cross-Coupling of C(sp3)-H Bonds with Arylsilanes. J. Am. Chem. Soc. 2015137, 4618-4621.

9. He, J.; Shigenari, T.; Yu, J.-Q. Palladium(0)/PAr3-Catalyzed Intermolecular Amination of C(sp3)-H Bonds: Synthesis of β-Amino Acids. Angew. Chem. Int. Ed. 201554, 6545-6549.

8. Chen, G.; Shigenari, T.; Jain, P.; Zhang, Z.; Jin, Z.; He, J.; Li, S.; Mapelli, C.; Miller, M. M.; Poss, M. A.; Scola, P. M.; Yeung, K.-S.; Yu, J.-Q. Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary. J. Am. Chem. Soc.2015137, 3338-3351.

7. Zhu, D.; Yang, G.; He, J.; Chu, L.; Chen, G.; Gong, W.; Chen, K.; Eastgate, M.; Yu, J.-Q. Ligand-Promoted Ortho-C-H Amination with Pd Catalysts. Angew. Chem. Int. Ed. 201554, 2497-2500.

6. Zhu, R.-Y.; He, J.; Wang, X.-C.; Yu, J.-Q. Ligand-Promoted Alkylation of C(sp3)-H and C(sp2)-H Bonds. J. Am. Chem. Soc.2014136, 13194-13197.

5. Deng, Y.; Gong, W.; He, J.; Yu, J.-Q. Ligand-Enabled Triple C-H Activation Reactions: One-Pot Synthesis of Diverse 4-Aryl-2-Quinolinones from Propionamide. Angew. Chem. Int. Ed. 201453, 6692-6695.

4. He, J.; Li, S.; Deng, Y.; Fu, H.; Laforteza, B. N.; Spangler, J. E.; Homs, A.; Yu, J.-Q. Ligand-Controlled C(sp3)-H Arylation and Olefination in Synthesis of Unnatural Chiral α-Amino Acids. Science 2014343, 1216-1220.

3. He, J.; Wasa, M.; Chan, K. S. L.; Yu, J.-Q. Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds. J. Am. Chem. Soc.2013135, 3387-3390.

2. Wasa, M.; Chan, K. S. L.; Zhang, X.-G.; He, J.; Miura, M.; Yu, J.-Q. Ligand-Enabled Methylene C(sp3)-H Bond Activation with a Pd(II) Catalyst. J. Am. Chem. Soc. 2012134, 18570-18572.

1. He, J.; Lu, Z.; Chai, G.; Fu, C.; Ma, S. CuCl-Catalyzed Stereoselective Conjugate Addition of Grignard Regents to 2,3-Allenoates. Tetrahedron 201268, 2719-2724.