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吕雷阳 副教授    


个人情况:

男,1989.6生,山东省,中共党员

Emaillvleiyang2008@ruc.edu.cn

Tel18001098633(微信同号)


学习、工作经历:

2020/9—至今,            副教授                   中国人民大学 化学系

2017/92020/8         博士后                  McGill University/兰州大学               导师 李朝军 教授

2012/92017/7,            博士                      中国人民大学(直博)                          导师 李志平 教授

2008/92012/7         学士                      青岛科技大学                                      导师 李明 教授


研究方向:

绿色合成化学(无金属催化)

有机氟化学

自由基串联反应及应用

过渡金属催化的C-H功能化及交叉偶联反应


获得奖项:

博士后创新人才支持计划(2017年)

博士生国家奖学金 (2014年,2015)

光华奖学金 (2016)

中国人民大学博士生一等奖学金 (5次,2012-2016)

中国人民大学第十届“学术新星”奖 (2016)

第十四届全国均相催化“优秀学生报告奖”(2015)


学术成绩:

本人在有机合成方法学、绿色合成化学及天然产物全合成等领域研究较为深入。在有机合成方法学方面,研究了Pd/NHC催化谐二氟环丙烷作为新型氟代烯丙基物种的反应性开发及应用;在天然产物全合成方面,先后实现了生物碱Asteropusazole AOlivacine以及抗癌活性药物Clavilactone AClavilactone B的全合成,而且首次完成了文献报道结构Clavilactone D的合成并纠正了分离文献中的结构错误;在绿色化学方面,系统地研究了NiPdRu催化新型碳负离子等价物腙(羰基化合物极性翻转生成)在交叉偶联反应中的应用、肼作为无痕还原剂在还原偶联反应中的应用以及光催化的新型化学转化。目前以第一/共一/通讯作者在Nat. Commun.2篇), Angew. Chem. Int. Ed.6篇), Chem. Sci.2篇), ACS Catal.3篇)等发表学术论文40余篇。

代表性论文:

[1]      Qian, H.; Nguyen, H. D.; Lv, L.*; Chen, S.*; Li, Z.* Chemo-, Stereo- and Regioselective Fluoroallylation/Annulation of Hydrazones with gem-Difluorocyclopropanes via Tunable Palladium/NHC Catalysis. Angew. Chem. Int. Ed. 2023, e202303271.

[2]      Lv, L.*; Qian, H. Developments and Applications of Allyl-(aza)allyl Coupling Reactions. Green Synth. Catal. 2023, DOI: 10.1016/j.gresc.2023.01.006.

[3]      Shu, S.; Wang, L.; Lv, L.*; Li Zhiping *.Copper-Catalyzed [3+2] Annulation of Pyridinium Ylides with α-CF3 Ketones: Synthesis of Functionalized 2-Fluoroindolizines. Asian J. Org. Chem. 2023, e202300075.

[4]      Lv, L.*; Qian, H.; Crowell, A. B.; Chen, S.*; Li, Z.* Pd/NHC-Controlled Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes with Allylboronates. ACS. Catal. 2022, 12, 6495-6505.

[5]      Lv, L.*; Qian, H.; Li, Z.* Catalytic Diversification of gem-Difluorocyclopropanes: Recent Advances and Challenges. ChemCatChem 2022, 14, e202200890.

[6]      Liu, F.; Lv, L.*; Ma, Y.*; Li, Z.* Copper-Catalyzed Radical Difluoromethylation-Peroxidation of Alkenes: Synthesis of β-Difluoromethyl. Peroxides. Asian J. Org. Chem. 2022, 11, e202200393.

[7]      Wang, L.; Shu, S.; Lv, L.*; Li, Z.* Copper-Catalyzed Remote Trifluoromethylthiolation-Peroxidation of Unactivated Alkenes via 1,5-Hydrogen Atom Transfer. Tetrahedron Lett. 2022, 104, 154029.

[8]      Gao, G.; Mao, K.; Lv, L.*; Li, Z.* Three-Component Coupling of α-Trifluoromethyl Carbonyls, Azides and Amines for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles. Adv. Synth. Catal. 2022, 364, 1402-1408.

[9]      Luo, Y.; Xu, B.; Lv, L.*; Li, Z.* Copper-Catalyzed Three-Component Germyl Peroxidation of Alkenes. Org. Lett. 2022, 24, 2425-2430.

[10]   Luo, Y.; Lv, L.*; Li, Z.* Copper-Catalyzed Germyl-Azidation of Alkenes with Germanium Hydrides and Trimethylsilyl Azide. Org. Lett. 2022, 24, 8052-8056.

[11]   Ma, Y.; Lv, L.*; Li, Z.* β-Perfluoroalkyl Peroxides as Fluorinated C3-Building Blocks for the Construction of Benzo[4,5]imidazo[1,2-a]pyridines. J. Org. Chem. 2022, 87, 1564-1573.

[12]   Wang, L.; Lv, L.*; Li, Z.* Concomitant Functionalization of Two Different Ketones by Merging Brønsted Acid Catalysis and Radical Relay Coupling. Org. Chem. Front. 2022, 9, 1561-1566.

[13]   Lv, L.*; Qian, H.; Ma, Y.; Huang, S.; Yan, X.; Li, Z.* Ligand-Controlled Regioselective and Chemodivergent Defluorinative Functionalization of gem-Difluorocyclopropanes with Simple Ketones. Chem. Sci. 2021, 12, 15511-15518. (Hot paper)

[14]   Lv, L.; Gao, G.; Luo, Y.; Mao, K.; Li, Z.* Three-Component Reactions of Alpha-CF3 Carbonyls, NaN3, and Amines for the Synthesis of NH-1,2,3-Triazoles. J. Org. Chem. 2021, 86, 17197-17212.

[15]   Lou, C.; Wang, X.; Lv, L.*; Li, Z.* Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides. Org. Lett. 2021, 23, 7608-7612.

[16]   Luo, Y.; Tian, T.; Nishihara, Y.; Lv, L.*; Li, Z.* Iron-Catalysed Radical Cyclization to Synthesize Germanium-Substituted Indolo[2,1-a]isoquinolin-6(5H)-ones and Indolin-2-ones. Chem. Commun. 2021, 57, 9276-9279.

[17]   Wang, X.; Lou, C.; Lv, L.*; Li, Z.* Annulative pi-Extension (APEX) of Indoles to Pyrido[1,2-a]indoles Using 4-Oxo Peroxides as C4 Units. Org. Lett. 2021, 23, 5978-5982.

[18]   Ma, Y.; Chen, Y.; Lv, L.*; Li, Z.* Regioselective Synthesis of Emission Color‐Tunable Pyrazolo[1,5‐a]pyrimidines with β,β‐Difluoro Peroxides as 1,3‐Bis‐Electrophiles. Adv. Synth. Catal. 2021, 363, 3233-3239.

[19]   Wang, L.; Ma, Y.; Jiang, Y.; Lv, L.*; Li, Z.* A Mn-Ratalyzed Remote C(sp(3))-H bond Peroxidation Triggered by Radical Trifluoromethylation of Unactivated Alkenes. Chem. Commun. 2021, 57, 7846-7849.

[20]   Lv, L.*; Li, C.-J.* Pd-Catalyzed Defluorinative Alkylation of gem-Difluorocyclopropanes: Switching Regioselectivity via Simple Hydrazones. Angew. Chem. Int. Ed. 2021, 60, 13098-13104.

[21]   Li, L.; Huang, S.; Mao, K.; Lv, L.*; Li, Z.* Synthesis of Isoxazoles via Cyclization of β-Fluoro Enones with Sodium Azide. Tetrahedron. Lett. 2021, 71, 153052.

[22]   Lv, L.*; Li, C.-J.* Ruthenium Catalyzed β-Selective Alkylation of Vinylpyridines with Aldehydes/Ketones via N2H4 Mediated Deoxygenative Couplings. Chem. Sci. 2021, 12, 2870-2875.

[23]   Tian, T.; Wang, X.; Lv, L.*; Li, Z.* Iron-Catalyzed Acylation-Functionalization of Unactivated Alkenes with Aldehydes. Chem. Commun. 2020, 56, 14637-14640.

[24]   Yu, L.; Lv, L.; Qiu, Z.; Chen, Z.; Tan, Z.; Liang, Y.-F.; Li, C.-J. Pd-Catalyzed Formal Hydroalkylation of Aryl-Substituted Alkynes with Hydrazones. Angew. Chem. Int. Ed. 2020, 59, 14009-14013. (contributed equally) (Hot paper)

[25]   Lv, L.; Yu, L.; Qiu, Z.; Li, C.-J. Switch in Selectivity for the Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones. Angew. Chem. Int. Ed. 2020, 59, 6466-6472. (VIP paper)

[26]   Lv, L.; Zhu, D.; Li, C.-J. Direct Dehydrogenative Alkyl Heck-Couplings of Vinylarenes with Umpolung Aldehydes Catalyzed by Nickel. Nat. Commun. 2019, 10, 715.

[27]   Lv, L.; Qiu, Z.; Li, J.; Liu, M.; Li, C.-J. N2H4 as Traceless Mediator for Homo- and Cross- Aryl Coupling. Nat. Commun. 2018, 9, 4739.

[28]   Lv, L.; Zhu, D.; Tang, J.; Qiu, Z.; Li, C.-C.; Gao, J.; Li, C.-J. Cross-Coupling of Phenol Derivatives with Umpolung Aldehydes Catalyzed by Nickel. ACS Catal. 2018, 8, 4622-4627.

[29]   Lv, L.; Zhu, D.; Qiu, Z.; Li, J.; Li, C.-J. Nickel-Catalyzed Regioselective Hydrobenzylation of 1,3-Dienes with Hydrazones. ACS Catal. 2019, 9, 9199-9205.

[30]   Zhu, D.; Lv, L.; Li, C.-C.; Ung, S.; Gao, J.; Li, C.-J. Umpolung of Carbonyls as Alkyl Organometallic Reagent Surrogates for Palladium Catalyzed Allylic Alkylation. Angew. Chem. Int. Ed. 2018, 57, 16520-16524. (contributed equally)

[31]   Zhou, Z.-Z.; Liu, M.; Lv, L.; Li, C.-J. Silver (I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage. Angew. Chem. Int. Ed. 2018, 57, 2616-2620. (contributed equally)

[32]   Lv, L.*; Li, Z. * FeCl3-Catalyzed Regio-Divergent Carbosulfenylation of Unactivated Alkenes: Construction of Medium-Sized Ring. J. Org. Chem. 2018, 83, 10985-10994.

[33]   Lv, L.; Li, Z. Iron-Catalyzed Oxidative Cyclization of 1,6-Enones with Aldehydes: Synthesis of Functionalized 3,4-Dihydro-2H-pyrans. Chin. J. Chem. 2017, 35, 303-306.

[34]   Lv, L.; Li, Z. Cycloalkylation of C(sp3)-H Bond with Neighboring Carboxylic Acid as Traceless Activating Group. J. Org. Chem. 2017, 82, 2689-2702.

[35]   Lv, L.; Snider, B. B.; Li, Z. Total Synthesis and Structure Revision of (±)-Clavilactone D Through Selective Cyclization of an α,β-Dicarbonyl Peroxide. J. Org. Chem. 2017, 82, 5487-5491.

[36]   Lv, L.; Lu, S.; Chen, Y.; Li, Z. Diastereoselective Building up Polycyclic Tetrahydrofurans via Tandem Annulation of 1,n-Enynes with Aliphatic Acids. Org. Chem. Front. 2017, 4, 2147-2152.

[37]   Lv, L.; Li, Z. Iron-Catalyzed Radical [2+2+2] Annulation of Benzene-Linked 1,7-Enynes with Aldehydes: Fused Pyran Compounds. Org. Lett. 2016, 18, 2264-2267.

[38]   Lv, L.; Bai, X.; Yan, X.; Li, Z. Iron-Catalyzed Decarbonylation Initiated [2+2+m] Annulation of Benzene-Linked 1,n-Enynes with Aliphatic Aldehydes. Org. Chem. Front. 2016, 3, 1509-1513.

[39]   Lv, L.; Li, Z. Fe-Catalyzed Cross-Dehydrogenative Couplings. Top. Curr. Chem. (Z) 2016, 374, 38. (Invited review)

[40]   Lv, L.; Lu, S.; Guo, Q.; Shen, B.; Li, Z. Iron-Catalyzed Acylation-Oxygenation of Terminal Alkenes for the Synthesis of Dihydrofurans Bearing a Quaternary Carbon. J. Org. Chem. 2015, 80, 698-704.

[41]   Lv, L.; Xi, H.; Bai, X.; Li, Z. Iron-Catalyzed Convergent Radical Cyclization of Aldehydes with Two Alkenes to 3,4-Dihydropyrans. Org. Lett. 2015, 17, 4324-4327.

[42]   Lv, L.; Qi, L.; Guo, Q.; Shen, B.; Li, Z. Iron-Catalyzed Divergent Tandem Radical Annulation of Aldehydes with Olefins toward Indolines and Dihydropyrans. J. Org. Chem. 2015, 80, 12562-12571.

[43]   Lv, L.; Shen, B.; Li, Z. Total Synthesis of (+)-Clavilactones A, B, and Proposed D through Iron-Catalyzed Carbonylation–Peroxidation of Olefin. Angew. Chem. Int. Ed. 2014, 53, 4164-4167.

[44]   Kan, J.; Chen, Z.; Qiu, Z.; Lv, L.; Li, C.; Li, C.-J. Umpolung Carbonyls Enable Direct Allylation and Olefination of Carbohydrates. Sci. Adv. 2022, 8, eabm6840.

[45]   Li, C.-C.; Kan, J.; Qiu, Z.; Li, J.; Lv, L.; Li, C.-J. Synergistic Relay Reactions to Achieve Redox- Neutral a-Alkylation of Olefinic Alcohols with Ruthenium(II)-Catalysis. Angew. Chem. Int. Ed. 2020, 59, 4544-4549.

[46]   Yao, J.; Chen, Z.; Yu, L.; Lv, L.; Cao, D.; Li, C.-J. Palladium-Catalyzed Hydroalkylation of Methylenecyclopropanes with Simple Hydrazones. Chem. Sci. 2020, 11, 10759-10763.

[47]   Cao, D.; Chen, Z.; Lv, L.; Zeng, H.; Peng, Y.; Li, C.-J. Light-Driven Metal-Free Direct Deoxygenation of Alcohols under Mild Conditions. iScience, 2020, 23, 101419.

[48]   Tian, T.; Wang, X.; Lv, L.; Li, Z. Iron-Catalyzed [2+2+2]Annulation of Aliphatic Bridged 1,n- Enynes with Aldehydes for the Synthesis of Fused Pyrans. E. J. Org. Chem. 2020, 4425-4428.

[49]   Qiu, Z.; Lv, L.; Li, J.; Li, C.-C.; Li, C.-J. Direct Conversion of Phenols into Primary Anilines with Hvdrazine Catalyzed by Palladium. Chem. Sci. 2019, 10, 4775-4781.

[50]   Li, C.-J.; Huang, J.; Dai, X.-J.; Wang, H.; Chen, N.; Wei, W.; Zeng, H.; Tang, J.; Li, C.; Zhu, D.; Lv, L. An Old Dog with New Tricks: Enjoin Wolff-Kishner Reduction for Alcohol Deoxygenation and C-C Bond Formations. Synlett. 2019, 30, 1508-1524.

[51]   Zhu, D.Lv, L.; Qiu, Z.; Li, C.-J. Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl

Halides. J. Org. Chem. 2019, 84, 6312−6322

[52]   Tang, J.; Lv, L.; Dai, X.-J.; Li, C.-C.; Li, L.; Li, C.-J. Nickel-Catalyzed Cross-Coupling of Aldehydes with Aryl Halides via Hydrazone Intermediates. Chem. Commun. 2018, 54, 1750-1753.

[53]   Li, J. ; Zhu, D. ; Lv, L.; Li, C.-J. Radical Difluoromethylthiolation of Aromatics Enabled by Visible Light. Chem. Sci. 2018, 9, 5781-5786.

[54]   Liu, W. ; Liu, P.; Lv, L.; Li, C.-J. Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light. Angew. Chem. Int. Ed. 2018, 57, 13499-13503.

[55]   Bai, X.; Lv, L.; Li, Z. Copper-Catalyzed Tandem Trifluoromethylation-Cyclization of Olefinic Carbonyls: Synthesis of Trifluoromethylated 2,3-Dihydrofurans and 3,4-Dihydropyrans. Org. Chem. Front. 2016, 3, 804-808.

[56]   Zheng, X.; Lv, L.; Lu, S.; Wang, W.; Li, Z.; Benzannulation of Indoles to Carbazoles and Its Applications for Synthesis of Carbazole Alkaloids. Org. Lett. 2014, 16, 5156-5159.

[57]   Lou, C.; Lv, L.*; Li, Z.* Fe-Catalyzed Ring-Opening Reactions of Siloxy Cyclopropanes with Alkenes and TBHP: Synthesis of 4-Ester Peroxides. J. Organomet. Chem. 2022, 977, 122467.

[58]   Lou, C.; Lv, L.; Li, Z.* Mn-Catalyzed Ring-Opening Peroxidation of Cyclobutanols: A Method for the Synthesis of 4-Oxo Peroxides. Adv. Synth. Catal. 2022, 364, 3743-3748.

[59]   Mao, K.; Ma, Y.; Lv, L.; Li, Z.* [4+1] Cyclization of α-CF3 Carbonyls with Hydrazides: Synthesis of 1,3,4-Oxadiazoles under Ambient Conditions. Asian J. Org. Chem. 2022, 11, e202200334.

[60]   Ma, Y.; Mao, K.; Chen, Y.; Lv, L.; Li, Z.* Tandem Defluorination/Annulation of α-CF3 Carbonyls with Bis-Nucleophiles: Stereodivergent Synthesis of 2-Alkylidene-1,3-Heterocycles. Tetrahedron Lett. 2022, 100, 153902.