刘元红 研究员 

中国科学院上海有机化学研究所

金属有机化学国家重点实验室 

上海市零陵路345号,200032

电话: +86 21 54925135

传真: +86 21 64166128

邮箱: yhliu@sioc.ac.cn

教育:

1988.9 - 1992.7   郑州大学化学系,学士

1992.9 - 1995.7   郑州大学化学系,硕士

1997.4 - 2000.3   日本北海道大学药学部,博士 (导师:Prof. Tamotsu Takahashi)

工作经历:

2000.4 - 2000.12   日本北海道大学催化研究中心,日本学术振兴学会(JSPS)特别研究员

2001.1 - 2002.12   日本北海道大学催化研究中心,COE(center of excellence)研究员

2003.1 - 2003.9  日本北海道大学催化研究中心,博士后研究员

2003.10 - 现在   中科院上海有机化学研究所,研究员

研究领域:

  1. 金催化的高效串联反应:利用金催化的策略,发展基于官能团化的炔烃等分子体系的高效串联反应,实现具有潜在生物活性的碳环和杂环分子的合成。 

  2. 廉价金属镍催化的反应方法学研究:实现镍催化惰性C-X键的断裂与偶联反应,发展镍催化的基于烯烃或炔烃的转化反应新模式。 

  3. 有机硼化合物的合成及反应性能研究:发展过渡金属催化的有机硼化合物的合成新方法,探索有机硼化合物在偶联等反应中的应用。 

获奖及荣誉:

  • Thieme Chemistry Journals Award (2007)
  • The Distinguished Lectureship Award from The Chemical Society of Japan (2007)

职务:

课题组长

 

主要研究进展:

  1. 金催化的高效串联反应 

  利用金易于活化炔烃、烯烃和联烯,在反应中易于形成碳正离子、金卡宾等特点,集中探索金催化的各类串联反应如扩环反应,1,6-卡宾迁移反应以及偶联反应等,发展实用有效的有机合成新方法。 

 

  

    2. 廉价金属镍催化的反应方法学研究 

  镍存在较多的氧化态,在反应过程中存在多种价态的循环过程,且易于通过形成丰富的金属中间体如金属杂环、烯基镍等实现炔烃的转化反应。我们开展了涉及惰性C-X键的偶联反应及炔烃的官能团化反应等。 

 

  

    3. 有机硼化合物的合成及反应性能研究 

  利用过渡金属催化的硼化反应与其它反应相结合,开展含硼产物尤其是环化产物的合成等。 

 

 

近年发表论文:

1.   Ligand-Controlled Regiodivergent Cyanoboration of Internal Allenes by Copper Catalysis Hui Hu , Guo-Cui Ji , Linjuan Jiang , Siwei Bi, Yuan-Ye Jiang,* Yuanhong Liu* Angew. Chem. Int. Ed. 2022, doi.org/10.1002/anie.202210338.

2. Gold(III) or Gold(I)/Lewis-Acid-Catalyzed Substitution/Cyclization/1,2-Migration Reactions of Propargyl Alcohols with 3-Amino-benzo[d]isoxazoles: Synthesis of Pyrimidine Derivatives. Ali Wang, Mingduo Lu, Xin Xie, Yuanhong Liu* Org. Lett. 2022, 24, 2944-2949.

3.  Gold-Catalyzed Cyclization of Ynones Involving cis-Hydrofunctionalizations: Rapid Assembly of C-, O-, or S-Functionalized Pyrroles by a Single Methodology. Miaomiao Pei, Ali Wang, Xin Xie, Xiaoping Hu, Yuanhong Liu* Org. Lett. 2022, 24, 1541-1545.

4.   Copper-catalyzed ortho-alkenylation of quinolone N-oxides with alkynes. Linjuan Jiang, Hui Hub, Yuanhong Liu* Org. Chem. Front. 2022, 9, 2198-2203.

5.   Gold-Catalyzed Spirocyclization of Furan-ynones and Unexpected Skeleton Rearrangement of the Resulting Spirohydrofurans. Yulong Chen, Wei Xu, Xin Xie,* Miaomiao Pei, Mingduo Lu, Yaotong Wang, and Yuanhong Liu* Org. Lett. 2021, 23, 1090-1095.

6.   Gold-Catalyzed Oxidative Cyclization Involving Nucleophilic Attack to the Keto Group of α,α′-Dioxo Gold Carbene and 1,2-Alkynyl Migration: Synthesis of Furan-3-carboxylates. Ali Wang, Mingduo Lu, Yuanhong Liu* Org. Lett. 2021, 23, 6813-6818.

7.  Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines. Xiaoping Hu, Xin Xie, Yi Gan, Gaonan Wang, Yuanhong Liu* Org. Lett. 2021, 23, 1296-1301.

8.   Synthesis of ortho-Diamino-Functionalized 1-Arylnaphthalenes through Nickel-Catalyzed Cyclization of Ynamide-Benzylnitriles with Organoboronic Acids. Xiaoping Hu, Peizhuo Lv, Ninghui Zhang, and Yuanhong Liu* Org. Lett. 2021, 23, 7949-7954.

9.   Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones. Ninghui Zhang, Chunli Zhang, Xiaoping Hu, Xin Xie, Yuanhong Liu* Org. Lett. 2021, 23, 6004-6009.

10. Cascade Skeletal Rearrangement of Gold Carbene Intermediates: Synthesis of Medium-Sized Pyrimidine-Fused Benzolactones. Ali Wang, Xiaoping Hu, Xin Xie, Yuanhong Liu* Adv. Synth. Catal. 2021, 363, 3769-3774.

11. Copper-Catalyzed ortho-Functionalization of Quinoline N-Oxides with Vinyl Arenes. Hui Hu, Xiaoping Hu, Yuanhong Liu* Angew. Chem. Int. Ed. 2020, 59, 18975-18979.

12. Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2. Aiyou Xia, Peizhuo Lv, Xin Xie, Yuanhong Liu* Org. Lett. 2020, 22, 7842-7847.

13. Nickel-Catalyzed Homo- and Cross-Coupling of Allyl Alcohols via Allyl Boronates. Yi Gan, Hui Hu, Yuanhong Liu* Org. Lett. 2020, 22, 4418- 4423

14. Gold/Lewis acid catalyzed oxidative cyclization involving activation of nitriles. Ali Wang, Xin Xie, Chunli Zhang, Yuanhong Liu* Chem. Commun. 2020, 56, 15581-15584.

15. Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C-O and C-C Bond Cleavage. Yi Gan, Ninghui Zhang, Shaoxu Huang, Yuanhong Liu* Chin. J. Chem. 2020, 38, 1686-1690.

16. Synthesis of phospholes and 1,10-biphospholes mediated by zirconacyclopentadienes and PBr3. Chunxiang Qin, Xin Xie,* Gaonan Wang, Xueshun Jia,* Yuanhong Liu.* Tetrahedron Letters 2020, 61, 151388.

17. Benzofurazan N-Oxides as Mild Reagents for the Generation of α Imino Gold Carbenes: Synthesis of Functionalized 7-Nitroindoles. Wei Xu, Yulong Chen, Ali Wang, Yuanhong Liu* Org. Lett. 2019, 21, 7613-7618.

18. Nickel-catalyzed highly regioselective hydrocyanation of alkenes with Zn(CN)2. Gaonan Wang, Xin Xie, Wei Xu, Yuanhong Liu* Org. Chem. Front. 2019, 6, 2037-2042.

19. Ligandless nickel-catalyzed transfer hydrogenation of alkenes and alkynes using water as the hydrogen donor. Xiaoping Hu, Gaonan Wang, Chunxiang Qin, Xin Xie, Chunli Zhang, Wei Xu, Yuanhong Liu* Org. Chem. Front., 2019, 6, 2619-2623.

20. Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source. Aiyou Xia, Xin Xie, Xiaoping Hu, Wei Xu, Yuanhong Liu* J. Org. Chem. 2019, 84, 13841-13857.

21. Ligand-Controlled Regiodivergent Silylation of Allylic Alcohols by Ni/Cu Catalysis for the Synthesis of Functionalized Allylsilanes. Yi Gan, Wei Xu, Yuanhong Liu* Org. Lett. 2019, 21, 9652-9657.

22. Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source. Xingjie Zhang, Xin Xie, Yuanhong Liu* J. Am. Chem. Soc. 2018, 140, 7385-7389.

23. Gold(I)-Catalyzed Formal Intramolecular Dehydro-Diels-Alder Reaction of Ynamide-ynes: Synthesis of Functionalized Benzo[b]carbazoles. Wei Xu, Gaonan Wang, Xin Xie, Yuanhong Liu* Org. Lett. 2018, 20, 3273-3277.

24. Copper-Catalyzed Borylative Cyclization of o-(Cyano)phenyl Propargyl Carbonates: Synthesis of Functionalized 1-Naphthylamines. Meijun Xiong, Hui Hu, Xiaoping Hu, Yuanhong Liu* Org. Lett. 2018, 20, 3661-3665.

25. Gold-Catalyzed Oxidative Cyclizations of {o-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1H?Isochromenes and 2H?Pyrans. Jidong Zhao, Wei Xu, Xin Xie, Ning Sun, Xiangdong Li, Yuanhong Liu* Org. Lett. 2018, 20, 5461-5465.

26. Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2. Aiyou Xia, Xin Xie, Haoyi Chen, Jidong Zhao, Chunli Zhang, Yuanhong Liu* Org. Lett. 2018, 20, 7735-7739.

27. Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio- and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through Cyclodimerization of 1-Ethynyl-2-propenyl Esters. Jidong Zhao, Shuang Yang, Xin Xie, Xiangdong Li, Yuanhong Liu* J. Org. Chem. 2018, 83, 1287-1297.

28. Selective [5 + 1] and [5 + 2] Cycloaddition of Ynamides or Propargyl Esters with Benzo[d]isoxazoles via Gold Catalysis. Wei Xu, Jidong Zhao, Xiangdong Li, Yuanhong Liu* J. Org. Chem. 2018, 83, 15470-15485.

29. Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage. Yi Gan, Gaonan Wang, Xin Xie, Yuanhong Liu* J. Org. Chem. 2018, 83, 14036-14048.

30.  Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents. Gaonan Wang, Yi Gan, Yuanhong Liu* Chin. J. Chem. 2018, 36, 916-920.

31. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2,3-Benzodiazepine Scaffolds. Hui Hu, Xiaoping Hu, Ming Chen, Ning Sun, Yuanhong Liu* Chin. J. Org. Chem. 2018, 38, 190-199.

32. Gold-Catalyzed Cadiot-Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes. Xiangdong Li, Xin Xie, Ning Sun, Yuanhong Liu* Angew. Chem. Int. Ed. 2017, 56, 6994-6998.

33. Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2 + 2 + 2]Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes. Gaonan Wang, Xu You, Yi Gan, Yuanhong Liu* Org. Lett. 2017, 19, 110-113.

34. General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP. Xingjie Zhang, Aiyou Xia, Haoyi Chen, Yuanhong Liu* Org. Lett. 2017, 19, 2118-2121.

35. Gold-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with 4,5?Dihydro-1,2,4-oxadiazoles: Synthesis of Functionalized 4-Aminoimidazoles.Wei Xu, Gaonan Wang, Ning Sun, Yuanhong Liu* Org. Lett. 2017, 19, 3307-3310.

36. Copper-Catalyzed Borylative Cyclization of in Situ Generated o-Allenylaryl Nitriles with Bis(pinacolato)diboron. Meijun Xiong, Xin Xie, Yuanhong Liu* Org. Lett. 2017, 19, 3398-3401.

37. PBr3-Mediated Cyclization of 1,7-Diyn-3,6-bis(propargyl carbonate)s: Synthesis of 5-Bromotetracenes. Ning Sun, Haoyi Chen, Xiangdong Li, Murong Xu, Yi Gan, Liangwei Zhang, Yuanhong Liu* J. Org. Chem. 2017, 82, 10051-10061.

38. Base-Catalyzed Cyclization of 1,6-Diynyl Carboxylates Involving Propargyl-Allenyl Isomerization: Efficient Synthesis of Benzo[b]fluorene and Its Analogues. Ning Sun, Xin Xie, Gaonan Wang, Haoyi Chen, Yuanhong Liu* Adv. Synth. Catal. 2017, 359, 1394-1401.

39. Synthesis of functionalized indolizines via gold(I)-catalyzed intramolecular hydroarylation/aromatization of pyrrole-ynes. Xiangdong Li, Jidong Zhao, Xin Xie, Yuanhong Liu* Org. Biomol. Chem., 2017, 15, 8119-8133.

40. Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines. Xu You, Xin Xie, Gaonan Wang, Meijun Xiong, Renhong Sun, Haoyi Chen, Yuanhong Liu* Chem. Eur. J. 2016, 22, 16765-16769.

41. Gold-Catalyzed Cyclization of Furan-Ynes bearing a Propargyl Carbonate Group: Intramolecular Diels-Alder Reaction with In Situ Generated Allenes. Ning Sun, Xin Xie, Haoyi Chen, Yuanhong Liu* Chem. Eur. J. 2016, 22, 14175-14180.

42. Dioxazoles, a new mild nitrene transfer in gold catalysis: highly efficient synthesis of functionalized oxazoles. Ming Chen, Ning Sun, Haoyi Chen Yuanhong Liu* Chem. Commun., 2016, 52, 6324-6327.

43. Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anticarbometalation of alkynes. Xingjie Zhang, Xin Xie, Yuanhong Liu* Chem. Sci., 2016, 7, 5815-5820.

44. Gold-catalyzed cyclization of 1,6-diynyl dithioacetals via 1,7-carbene transfer and aromatic C–H functionalization. Wei Xu, Ming Chen, Ning Sun, Yuanhong Liu* Chem. Commun., 2016, 52, 11000-11003.

45. Gold(I)-Catalyzed Cascade Hydroarylation/Cycloaromatization to Indolizines via Pyridine Ring Construction. Xiangdong Li, Xin Xie, and Yuanhong Liu* J. Org. Chem. 2016, 81, 3688-3699.

46. Gold-Catalyzed Oxidative Ring Expansion of 2-Alkynyl-1,2-Dihydropyridines or -quinolines: Highly Efficient Synthesis of Functionalized Azepine or Benzazepine Scaffolds Ming Chen, Yifeng Chen, Ning Sun, Jidong Zhao, Yuanhong Liu* Yuxue Li* Angew. Chem. Int. Ed. 2015, 54, 1200-1204.

47. Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring Expansion of Alkynyl Quinols. Jidong Zhao, Jun Liu, Xin Xie, Shi Li,* Yuanhong Liu* Org. Lett. 2015, 17, 5926-5929.

48. Cyano-Schmittel Cyclization through Base-Induced Propargyl-Allenyl Isomerization: Highly Modular Synthesis of Pyridine-Fused Aromatic Derivatives. Xu You, Xin Xie, Haoyi Chen, Yuxue Li,* Yuanhong Liu* Chem. Eur. J. 2015, 21, 18699-18705.

49. Gold-Catalyzed Ring Expansion of Alkynyl Heterocycles through 1,2-Migration of an Endocyclic Carbon–Heteroatom Bond. Ming Chen, Ning Sun, Wei Xu, Jidong Zhao, Gaonan Wang, Yuanhong Liu* Chem. Eur. J. 2015, 21, 18571-18575.

50. Insertion of Nitriles into Zirconocene-1-aza-1,3-diene Complexes: Chemoselective Synthesis of N-H and N-Substituted Pyrroles. Shasha Yu, Meijun Xiong, Xin Xie, Yuanhong Liu* Angew. Chem. Int. Ed. 2014, 53, 11596-11599.