Lei Jiao (焦雷)

Lei Jiao was born in Beijing, China in January 1983. He obtained his BSc in chemistry in 2005 at Peking University, and continued to study synthetic and computational organic chemistry there in the lab of Prof. Zhi-Xiang Yu. In 2010, after receiving his PhD, he performed postdoctoral research in the Thorsten Bach group at the Department of Chemistry, Technical University Munich with the support of the Humboldt Fellowship. After a 3-year research stay in Germany, he started his independent career as a principle investigator at the Center of Basic Molecular Science (CBMS), Department of Chemistry at Tsinghua University in 2014, and he has been an associate professor with tenure since 2022.

He is interested in mechanistic study on organic reactions, mechanism-based design and development of new reactions and catalytic systems, and their application in natural product synthesis. The research group is devoted to studying basic scientific problems in molecular transformation and solving challenging synthetic problems by rational design. At present, the major research areas include N-boryl pyridyl anion chemistry, novel ligand design, and synthesis of indole alkaloids.

Awards and Honors

  • CCS Physical Organic Chemistry Young Investigator Award (2023)
  • CCS Physical Organic Chemistry Newcomer Award (2017)
  • Qiushi Outstanding Young Scholar Award (2015)
  • Thieme Chemistry Journals Award (2014)
  • National Excellent Doctoral Dissertation (2012)
  • Eli Lilly Asia Outstanding Graduate Thesis Award (2010)
  • Roche Chemical Innovation Award (2008)

Professional Activities

  • 2023- Advisory Board, SYNTHESIS
  • 2019- Professional Committee of Physical Organic Chemistry, Chinese Chemical Society

Invited Talks

  • 4th National Organic Radical Chemistry Conference, Xiamen, China (2024/04)
  • 2023 International Conference on Photochemistry and Industry, Wuhan, China (2023/10)
  • 4th Chinese Chemical Society Conference on Boron Chemistry, Fuzhou, China (2023/09)
  • Annual Meeting of Japanese Photochemistry Association, Hiroshima, Japan (2023/09)
  • 3rd Workshop on Radical and Electron Transfer Reactions, Osaka, Japan (2023/09)
  • 15th National Conference on Physical Organic Chemistry, Lanzhou, China (2023/07)
  • 10th Pacific Symposium on Radical Chemistry (PSRC10), Kyoto, Japan (2023/06)
  • Lecture at Department of Chemistry, SUSTech (2023/04)
  • 12th National Conference on Organic Chemistry, Hefei, China (2022/09)
  • 3rd National Conference on Organic Radical Chemistry, Wuhan, China (2022/08)
  • 25th IUPAC International Conference on Physical Organic Chemistry, Hiroshima, Japan (2022/07)
  • NTU Chemistry Virtual Seminar, Nanyang Technological University, Singapore (2021/09)
  • 9th China-Korea Symposium on Organic Chemistry, Kunming, China (2019/12)
  • 1st International Symposium on Molecular Recognition and Synthesis, Shanghai, China (2019/10)
  • 10th National Conference on Organic Chemistry, Shanghai, China (2019/09)
  • 2nd International Symposium on Organic Reaction Mechanism, Shenzhen, China (2018/05)
  • 31th Chinese Chemical Society Congress, Physical Organic Session, Hangzhou, China (2018/05)
  • 10th National Conference on Organic Chemistry, Shenzhen, China (2017/12)
  • 12th National Conference on Physical Organic Chemistry, Wuhan, China (2017/10)
  • 6th Sino-German Frontiers of Chemistry Symposium, Shanghai, China (2016/08)
  • 30th Chinese Chemical Society Congress, Physical Organic Session, Dalian, China (2016/07)

Contact

Address: RM S907, Mong Man Wai Building of Science and Technology
                 Center of Basic Molecular Science, Department of Chemistry
                 Tsinghua University, Beijing 100084, China

E-mail: leijiao@mail.tsinghua.edu.cn

Phone: +86-10-6278-8874

Publications

  1. Shixue Zhang, Liang Cheng, Jian-Qing Qi, Zongbin Jia, Long Zhang, Lei Jiao*, Xingwei Guo*, Sanzhong Luo* "Direct Observation of Enamine-Derived Radicals with Time-Resolved Electron Paramagnetic Resonance." CCS Chem. 2024, doi:10.31635/ccschem.024.202404035.
  2. Jian-Qing Qi, Weiqun Suo, Jing Liu, Songtao Sun, Lei Jiao*, Xingwei Guo* "Direct Observation of All Open-Shell Intermediates in a Photocatalytic Cycle." J. Am. Chem. Soc. 2024, 146, 7140-7145.
  3. Lutao Bai, Lei Jiao* "Photoinduced Radical Borylation of Alkyl Chlorides." Eur. J. Org. Chem. 2024, e202400043.
  4. Feng-Yuan Wang, Lei Jiao* "Thio-Cyclopentene Ligands for Catellani-Type Reactions." Encyclopedia of Reagents for Organic Synthesis (EROS), doi:10.1002/047084289X.rn02570.
  5. Chen-Hui Yuan, Xiao-Xia Wang, Keyun Huang, Lei Jiao* "Unveiling the Mechanistic Role of Chiral Palladacycles in Pd(II)-Catalyzed Enantioselective C(sp3)-H Functionalization." ChemRxiv 2024, doi:10.26434/chemrxiv-2024-1rw6m.
  6. Chen-Hui Yuan, Lei Jiao* "Ligand-Enabled Palladium(II)-Catalyzed γ-C(sp3)−H Arylation of Primary Aliphatic Amines." Org. Lett. 2024, 26, 29-34.
  7. Fei-Yu Zhou, Lei Jiao* "4-Pyridyl Perfluoroalkyl Sulfide as a Practical Nucleophilic Perfluoroalkylation Reagent." ChemRxiv 2023, doi:10.26434/chemrxiv-2023-l3lhp.
  8. Shixue Zhang, Shengqi Zhou, Jian-Qing Qi, Lei Jiao, Xingwei Guo* "Time-Resolved Electron Paramagnetic Resonance Spectrometer Based on Ultrawide Single-Sideband Phase-Sensitive Detection." Rev. Sci. Instrum. 2023, 94, 084101.
  9. Lutao Bai, Lei Jiao* "Modular Photoredox System with Extreme Reduction Potentials Based on Pyridine Catalysis." Chem 2023, 9, 3245-3267.
  10. Xinyu Xu, Lei Jiao* "The Stereochemistry of the Reactions between Palladacycle Complexes and Primary Alkyl Iodides." Organometallics 2023, 42, 606-614.
  11. Chen-Hui Yuan, Xiao-Xia Wang, Lei Jiao* "Ligand-Enabled Pd(II)-Catalyzed Enantioselective β-C(sp3)-H Arylation of Aliphatic Tertiary Amides." Angew. Chem. Int. Ed. 2023, 62, e202300854.
  12. Feng-Yuan Wang, Yu-Xiu Li, Lei Jiao* "Functionalized Cycloolefin Ligand as a Solution to Ortho-Constraint in the Catellani-Type Reaction." J. Am. Chem. Soc. 2023, 145, 4871-4881.
  13. Fei-Yu Zhou, Lei Jiao* "Asymmetric Defluoroallylation of 4-Trifluoromethylpyridines Enabled by Umpolung C-F Bond Activation." Angew. Chem. Int. Ed. 2022, 61, e202201102.
  14. Ya-Xin Zheng, Lei Jiao* "Hybrid Cycloolefin Ligands for Palladium/Olefin Cooperative Catalysis." Nature Synthesis 2022, 1, 180-187.
  15. Dong Gao, Lei Jiao* "Divergent Synthesis of Indolenine and Indoline Ring Systems by Palladium-Catalyzed Asymmetric Dearomatization of Indoles." Angew. Chem. Int. Ed. 2022, 61, e202116024.
  16. Dong Gao, Lei Jiao* "Construction of Indoline/Indolenine Ring Systems by a Palladium-Catalyzed Intramolecular Dearomative Heck Reaction and the Subsequent Aza-Semipinacol Rearrangement." J. Org. Chem. 2021, 86, 5727-5743.
  17. Feng-Yuan Wang, Lei Jiao* "Total Synthesis of (-)-Arborisidine." Angew. Chem. Int. Ed. 2021, 60, 12732-12736.
  18. Fei-Yu Zhou, Lei Jiao* "Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines." Synlett 2021, 32, 159-178.
  19. Tan-Hao Shi, Shuo Tong, Lei Jiao*, Mei-Xiang Wang* "A Theoretical Study on the Macrocyclic Strain of Zigzag Molecular Belts." Organic Materials 2020, 2, 300-305.
  20. Jian-Qing Qi, Lei Jiao* "DFT Study on the Mechanism of 4,4′-Bipyridine-Catalyzed Nitrobenzene Reduction by Diboron(4) Compounds." J. Org. Chem. 2020, 85, 13877-13885.
  21. Yu-Jie Wang, Chen-Hui Yuan, De-Zhao Chu, Lei Jiao* "Regiocontrol in the Oxidative Heck Reaction of Indole by Ligand-Enabled Switch of the Regioselectivity-Determining Step." Chem. Sci. 2020, 11, 11042-11054.
  22. Huan Yang, Li Zhang, Fei-Yu Zhou, Lei Jiao* "An Umpolung Approach to the Hydroboration of Pyridines: A Novel and Efficient Synthesis of N-H 1,4-Dihydropyridines." Chem. Sci. 2020, 11, 742-747.
  23. Li Zhang, Zhong-Qian Wu, Lei Jiao* "Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine." Angew. Chem. Int. Ed. 2020, 59, 2095-2099.
  24. Zongyang Li, Shiyang Xu, Baoliang Huang, Chenhui Yuan, Wenxu Chang, Bin Fu, Lei Jiao*, Peng Wang, Zhenhua Zhang* "Pd-Catalyzed Carbonylation of Acyl Azides." J. Org. Chem. 2019, 84, 9497-9508.
  25. Li Zhang, Lei Jiao* "Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides." J. Am. Chem. Soc. 2019, 141, 9124-9128.
  26. Xufang Liu, Wei Zhang, Yujie Wang, Ze-Xin Zhang, Lei Jiao*, Qiang Liu* "Cobalt-Catalyzed Regioselective Olefin Isomerization Under Kinetic Control." J. Am. Chem. Soc. 2018, 140, 6873-6882.
  27. Huan Yang, De-Zhao Chu, Lei Jiao* "Aromatization Modulates the Activity of Small Organic Molecules as Promoters for Carbon– Halogen Bond Activation." Chem. Sci. 2018, 9, 1534-1539.
  28. Yu-Jie Wang, Wei-Tang Li, Lei Jiao* "A Convenient Method for the Direct Acquisition of Kinetic Rate Data for Catalytic Organic Reactions by Gas Uptake Measurements." Asian J. Org. Chem. 2018, 7, 570-578.
  29. Hao-Yi Du, Si-Cong Chen, Xiao-Jun Su, Lei Jiao*, Ming-Tian Zhang* "Redox-Active Ligand Assisted Multielectron Catalysis: A Case of CoIII Complex as Water Oxidation Catalyst." J. Am. Chem. Soc. 2018, 140, 1557-1565.
  30. Li Zhang, Lei Jiao* "Super Electron Donors Derived from Diboron." Chem. Sci. 2018, 9, 2711-2722.
  31. Ze-Xin Zhang, Si-Cong Chen, Lei Jiao* "Asymmetric Total Synthesis of (+)-Minfiensine by an Asymmetric Cascade Cyclization Strategy." Synlett 2017, 28, 2199-2204.
  32. Huan Yang, Li Zhang, Lei Jiao* "N-Methylanilines as Simple and Efficient Promoters for Radical-Type Cross-Coupling Reactions of Aryl Iodides." Chem. – Eur. J. 2017, 23, 65-69.
  33. Li Zhang, Lei Jiao* "Pyridine-Catalyzed Radical Borylation of Aryl Halides." J. Am. Chem. Soc. 2017, 139, 607-610.
  34. Lei Jiao*, Kathrin Lang* "The 6th Sino–German Frontiers of Chemistry Symposium (Community Report)." Chem. - Asian. J. 2016, 11, 3292-3296.
  35. Li Zhang, Huan Yang, Lei Jiao* "Revisiting the Radical Initiation Mechanism of the Diamine-Promoted Transition-Metal-Free Cross-Coupling Reaction." J. Am. Chem. Soc. 2016, 138, 7151-7160.
  36. Ze-Xin Zhang, Si-Cong Chen, Lei Jiao* "Total Synthesis of (+)-Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization." Angew. Chem. Int. Ed. 2016, 55, 8090-8094.
  37. Lei Jiao, Thorsten Bach* "Regioselective Direct C-H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process" Synthesis 2014, 46, 35-41.
  38. Lei Jiao, Zhi-Xiang Yu* "Vinylcyclopropane Derivatives in Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Carbocyclic Compounds." J. Org. Chem. 2013, 78, 6842-6848.
  39. Lei Jiao, Thorsten Bach* "Palladium-Catalyzed Direct C-H Alkylation of Electron-Deficient Pyrrole Derivatives" Angew. Chem. Int. Ed. 2013, 52, 6080-6083.
  40. Lei Jiao, Eberhardt Herdtweck, Thorsten Bach* "Pd(II)-Catalyzed Regioselective 2-Alkylation of Indoles via a Norbornene-Mediated C–H Activation: Mechanism and Applications." J. Am. Chem. Soc. 2012, 134, 14563-14572.
  41. Lei Jiao, Thorsten Bach* "Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation" J. Am. Chem. Soc. 2011, 133, 12990-12993.
  42. Lei Jiao, Mu Lin, Zhi-Xiang Yu* "Density Functional Theory Study of the Mechanisms and Stereochemistry of the Rh(I)-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Ene- and 1-Yne-Vinylcyclopropanes." J. Am. Chem. Soc. 2011, 133, 447-461.
  43. Lei Jiao, Mu Lin, Lian-Gang Zhuo, Zhi-Xiang Yu* "Rh(I)-Catalyzed [(3 + 2) + 1] Cycloaddition of 1-Yne/Ene-vinylcyclopropanes and CO: Homologous Pauson−Khand Reaction and Total Synthesis of (±)-α-Agarofuran." Org. Lett. 2010, 12, 2528-2531.
  44. Lei Jiao, Mu Lin, Zhi-Xiang Yu* "Rh(I)-Catalyzed Intramolecular [3 + 2] Cycloaddition Reactions of 1-Ene-, 1-Yne- and 1-Allene-Vinylcyclopropanes." Chem. Commun. 2010, 46, 1059-1061.
  45. Yong Liang, Lei Jiao, Shiwei Zhang, Zhi-Xiang Yu*, Jiaxi Xu* "New Insights into the Torquoselectivity of the Staudinger Reaction." J. Am. Chem. Soc. 2009, 131, 1542-1549.
  46. Lei Jiao, Siyu Ye, Zhi-Xiang Yu* "Rh(I)-Catalyzed Intramolecular [3 + 2] Cycloaddition of trans-Vinylcyclopropane-enes." J. Am. Chem. Soc. 2008, 130, 7178-7179.
  47. Lei Jiao, Changxia Yuan, Zhi-Xiang Yu* "Tandem Rh(I)-Catalyzed [(5+2)+1] Cycloaddition/Aldol Reaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (±)-Hirsutene and (±)-1-Desoxyhypnophilin." J. Am. Chem. Soc. 2008, 130, 4421-4430.
  48. Lei Jiao, Yong Liang, Jiaxi Xu* "Origin of the Relative Stereoselectivity of the β-Lactam Formation in the Staudinger Reaction." J. Am. Chem. Soc. 2006, 128, 6060-6069.
  49. Lei Jiao, Qianfeng Zhang, Yong Liang, Shiwei Zhang, Jiaxi Xu* "A Versatile Method for the Synthesis of 3-Alkoxycarbonyl β-Lactam Derivatives." J. Org. Chem. 2006, 71, 815-818.
  50. Yong Liang, Lei Jiao, Shiwei Zhang, Jiaxi Xu* "Microwave- and Photoirradiation-Induced Staudinger Reactions of Cyclic Imines and Ketenes Generated from α-Diazoketones. A Further Investigation into the Stereochemical Process." J. Org. Chem. 2005, 70, 334-337.