余志祥

男， 北京大学化学院， 教授/研究员/教授级高工或同等级别

学习/工作经历

1987-1991, 武汉大学, 学士;
1994-1997, 北京大学, 硕士;
1997-2001, 香港科技大学, 博士;
2001-2004, 加州大学洛杉矶分校, 博士后;
2004-2008, 北京大学, 副教授, 博导, 理论和合成有机化学学术带头人, 独立课题研究组组长;
2008-现在, 北京大学, 教授, 博导, 理论和合成有机化学学术带头人。

研究领域和兴趣

理论和合成有机化学

主要业绩

主要从事于将理论计算和有机合成相结合来研究有机化学反应机理，发展有机合成方法，并将发展的有机合成方法应用于天然产物与药物分子的合成。目前已对Lu-[3+2]环加成反应, 金属催化环加成反应，卡宾的插入反应等十几种重要化学反应的机理进行研究; 从理论和实验上发现和验证了[1,2]-质子迁移过程需要水和其它质子给体作为催化剂的重要现象; 提出一种新的半定量的前线分子轨道方法来半定量地计算反应的活化能以及分子的亲核性和亲电性; 发展了合成不同环系的[3+2], [5+1], [3+2+1], [4+2+1], [7+1], [5+2+1]等成环反应并将其中的一些反应用于多个天然产物的合成。

代表成果

Studies of Mechanisms of Organic Reactions:

1. “An Unexpected Role of A Trace Amount of Water in Catalyzing Proton Transfer in Phosphine-Catalyzed (3+2) Cycloaddition of Allenoates and Alkenes”.
Yuanzhi Xia, Yong Liang, Yuanyuan Chen, Ming Wang, Lei Jiao, Feng Huang, Song Liu, Yahong Li, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2007, 129, 3470.

2. “Why Is Copper(I) Complex More Competent Than Dirhodium(II) Complex in Catalytic Asymmetric O−H Insertion Reactions? A Computational Study of the Metal Carbenoid O−H Insertion into Water”.
Yong Liang, Haolai Zhou, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2009, 131, 17783.

3. “A DFT Study of the Mechanisms and Stereochemistry of the Rh(I)-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Ene- and 1-Yne-Vinylcyclopropanes”
Lei Jiao, Mu Lin, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2011, 133, 447.

4. “A Frontier Molecular Orbital Theory Approach to Understanding the Mayr Equation and to Quantifying Nucleophilicity and Electrophilicity by Using HOMO and LUMO Energies”
Lian-Gang Zhuo, Wei Liao, and Zhi-Xiang Yu,* Asian J. Org. Chem., 2012, 1, 336.

5. “Kinetic or Dynamic Control on a Bifurcating Potential Energy Surface? An Experimental and DFT Study of Gold-Catalyzed Ring Expansion and Spirocyclization of 2‑Propargyl-β-tetrahydrocarbolines”
Lei Zhang, Yi Wang, Zhu-Jun Yao, Shaozhong Wang,* and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2015, 137, 13290.

6. “Mechanistic Study on Gold-Catalyzed Cycloisomerization of Dienediynes Involving Aliphatic C−H Functionalization and Inspiration for Developing a New Strategy to Access Polycarbocycles”
Yi Wang, Pei-Jun Cai, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2020, 142, 2777.

7. “Synergy of activating substrate and introducing C–H···O interaction to achieve Rh2(II)-catalyzed asymmetric cycloisomerization of 1,n-enynes”
Rui Wu, Kai Chen, Jun Ma, Zhi-Xiang Yu*, and Shifa Zhu,* Science China Chemistry, 2020, 63, 1230.

8, “Mechanism and Stereochemistry of Rhodium-Catalyzed [5 + 2 + 1] Cycloaddition of Ene−Vinylcyclopropanes and Carbon Monoxide Revealed by Visual Kinetic Analysis and Quantum Chemical Calculations” Yi Wang, Wei Liao, Yuanyuan Wang, Lei Jiao, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2022, 144, 2624.

9, “Kinetic, Thermodynamic, and Dynamic Control in Normal vs. Cross [2 + 2] Cycloadditions of Ene-Keteniminium Ions: Computational Understanding, Prediction, and Experimental Verification”
Pan Zhang, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2023, 145, 9634.

10, “Unprecedented endo-oxidative cyclometallation and [4 + 3] cycloaddition of diene-vinylcyclopropanes”
Jun Yang, Pan Zhang, Zeyuan Shen, Yi Zhou, and Zhi-Xiang Yu,* Chem. 2023, 9, 1477.

11, “Metalla-Claisen Rearrangement in Gold-Catalyzed [4+2] Reaction: A New Elementary Reaction Suggested for Future Reaction Design”
Jing Liu, Yusheng Yang, Weiming Shi, and Zhi-Xiang Yu,* Angew. Chem. Int. Ed. 2023, 63, e202217654.

12, “Selective Hydrofunctionalization of Alkenyl Fluorides Enabled by Nickel-Catalyzed Hydrogen Atoms and Group Transfer: Reaction Development and Mechanistic Study”
Fan Chen, Qianwei Zhang, Yingying Li, Zhi-Xiang Yu,* and Lingling Chu,* J. Am. Chem. Soc. 2024. 146, 11418.

13, “Involving Carbene or Not? Mechanism of Corey–Winter Reaction”
Pan Zhang, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2025, 147, 13915.

14, “Strained Dehydro-[2,2]-paracyclophane Enabled Planar Chirality Construction and [2.2]Paracyclophane Functionalization”
Xue Zhang, Yi Zhou, Zhi-Xiang Yu,* Chen-Ho Tung, and Zhenghu Xu,* Angew. Chem. Int. Ed. 2025, 64, e202420667.

15, “An Experimental and Theoretical Investigation into [2π + 2π] Cycloaddition Reactions Catalyzed by a Cationic Cobalt(I) Complex Containing a Strong-Field PCNHCP Pincer Ligand”
Tofayel Sheikh Mohammad, Yi Jin, Sakthi Raje, Katarzyna Młodzikowska-Pienko, ́ Zhi-Xiang Yu,* and Graham de Ruiter,* J. Am. Chem. Soc. 2025, 147, 15195.


Development of ring formation reactions and application in synthesis of natural products and pharmaceutical molecules:

16. “Conjugated Diene Assisted Allylic C-H Bond Activation: Cationic Rh(I) Catalyzed Syntheses of Polysubstituted Tetrahydropyrroles, Tetrahydrofurans, and Cyclopentanes from Ene-2-Dienes”
Qian Li, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2010, 132, 4542.

17，“Rhodium-Catalyzed [5 + 2 + 1] Cycloaddition of Ene–Vinylcyclopropanes and CO: Reaction Design, Development, Application in Natural Product Synthesis, and Inspiration for Developing New Reactions for Synthesis of Eight-Membered Carbocycles”
Yi Wang, and Zhi-Xiang Yu,* Acc. Chem. Res. 2015, 48, 2288.

18. “Rh(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize Bicyclo[4.3.1]decane Skeleton”
Cheng-Hang Liu, and Zhi-Xiang Yu,* Angew. Chem. Int. Ed. 2017, 56, 8667.

19. “Rh-Catalyzed [4+2+1] Cycloaddition of in situ Generated Ene/Yne-Ene-Allenes and CO”
Zi-You Tian, Qi Cui, Cheng-Hang Liu, and Zhi-Xiang Yu,* Angew. Chem. Int. Ed. 2018, 57 15544.

20, “Dual Activation Strategy to Achieve C–C Cleavage of Cyclobutanes: Development and Mechanism of Rh and Zn Cocatalyzed [4 + 2] Cycloaddition of Yne-Vinylcyclobutanones”
Guan-Yu Zhang, Pan Zhang, Bing-Wen Li, Kang Liu, Jun Li, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2022, 144, 21457.

21, “Strain-Release-Controlled [4 + 2 + 1] Reaction of Cyclopropyl-Capped Diene-ynes/Diene-enes and Carbon Monoxide Catalyzed by Rhodium”.
Chen-Long Li, Yusheng Yang, Yi Zhou, Zhao-Chen Duan, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2023, 145, 5496.

22, “Rh-Catalyzed [4+1] Reaction of Cyclopropyl-Capped Dienes (but not Common Dienes) and Carbon Monoxide: Reaction Development and Mechanistic Study”
Yusheng Yang, Han-Xiao Li, Tian-Yu Zhu, Zi-You Zhang, and Zhi-Xiang Yu,* J. Am. Chem. Soc. 2023, 145, 17087.

23, “Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature”
Han-Xiao Li, and Zhi-Xiang Yu,* Org. Lett. 2024. 26, 3458.

24, “Ni(0)-Catalyzed Rearrangement of Vinylcyclobutanones (VCBOs) to Synthesize Six-Membered Non-Conjugated Enones”
Jiguo Ma, Jicheng Duan, and Zhi-Xiang Yu,* Angew. Chem. Int. Ed. 2024, e202417407.

25, “Rhodium-Catalyzed [5 + 1 + 2] Cycloaddition of Yne-3-acyloxy-1,4- enynes (YACEs) and Carbon Monoxide: Reaction Development and Mechanism”
Qi Cui, Pan Zhang, Bing-Wen Li, Yi Jin, Qianwei Zhang, Hong-Xi Bai, and Zhi-Xiang Yu,* ACS Catal. 2024, 14, 14595.

26, “Rh-Catalyzed [8+1] Cycloaddition of Vinyl Biscyclopropanes with CO for the Synthesis of Nine-Membered Carbocycles”
Yi Zhou, Yi Jin, Xinxuan Li, Xi-Jia Liu, Yi Wang, and Zhi-Xiang Yu,* ACS Catal. 2025, 15, 4441.

27, “Vinylcyclopropanes as Three-Carbon Synthons in Rhodium-Catalyzed Cycloadditions: Reaction Development, Mechanistic Studies, New Inspirations, and Synthetic Applications”
Pan Zhang, and Zhi-Xiang Yu,* Acc. Chem. Res. 2025, 58, 1065.

28, “Rhodium-Catalyzed 1,5-Sigma Migratory Ring Expansion of gem-Difluorodienyl-Cyclopropanes and Cyclobutanes”
Zhiqiang Huang, Sixuan Zhao, and Zhi-Xiang Yu,* Angew. Chem. Int. Ed. 2025, e202500074.

29, “Rhodium-Catalyzed [5 + 1 + 2] Reaction of Yne-Vinylcyclopropenes and CO: The Application of Vinylcyclopropenes for Higher-Order Cycloaddition”
Zhiqiang Huang, and Zhi-Xiang Yu,* J. Am. Chem. Soc.. 2025, 147, 15947.

30, “Rh-Catalyzed trans-Divinylcyclopropane Rearrangement: AnApproach to 1,5-Disubstituted 1,4-Cycloheptadienes”
Han-Xiao Li, Zeyuan Shen, Jiguo Ma, and Zhi-Xiang Yu,* Org. Lett. 2024. 26, 3458.

*以上信息由高级会员个人更新和维护。