General

Prof. Qilong Shen

Key Laboratory of Organofluorine Chemistry

Shanghai Institute of Organic Chemistry

345 Lingling Lu, Shanghai, 200032

Telephone: 21-54925197

Email: shenql@sioc.ac.cn
Telephone: 21-54925197

Research Areas

Organofluorine Chemistry: Electrophilic fluoroalkylation reagents and their reactions

Organometallics: transition metal-catalyzed reaction, mechanistic study including isolation of the key intermediate, kinetics

Material Science: living-polymerization of fluorinated monomer

Education


1992-1996, Department of Environmental Science and Engineering, Nanjing University, China, Bachelor

1996-1999, Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Master

2000-2002, Chemistry Department, University of Massachusetts, Dartmouth, Master

2002-2007, Chemistry Department, Yale University, PhD



Honors & Distinctions

2010, Hundreds Talens Program of SIOC

2011, Pujiang Program of Shanghai

2013, Thieme Chemitry Journal Award

2015, Asia Core Program Lectureship Award

2016, The National Science Fund for Distinguished Young Scholars


Publications

1.       Shao, X.-X.; Xu, C.-F; Lu, L.; Shen, Q.* “Shelf-Stable Electrophilic Reagents for Trifluoromethylthiolation” Acc. Chem. Res. 2015, 48, 1227


2.       Gu, Y.; Leng, X.-B.; Shen, Q.* “Cooperative Dual Palladium/Silver Catalyst for Direct Difluoromethylation of aryl Bromides and Iodides” Nat. Commun. 2014, 5, 5405, doi: 10.1038/ncomms6405


3.       Zhu, D.-H.; Gu, Y.; Lu, L.*; Shen, Q.* “N-Difluoromethylthiophthalimide: A Shelf-Stable Electrophilic Regent for Difluoromethylthiolation” J. Am. Chem. Soc. 2015, 137, 10547.


4.       Qi, Q.-Q.; Shen, Q.;* Lu, L.* “Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature” J. Am. Chem. Soc. 2012, 134, 6548

 

5.       Zhu, J.-S.; Liu, Y.-F.; Shen, Q.* “Direct of Difluoromethylation of Alcohols with an Electrophilic Difluoromethylated Sulfonium Ylide” Angew. Chem. Int. Ed. 2016, 55, 9050

 

6.       Wu, J.; Gu, Y.; Leng, X.-B.; Shen, Q.* “Copper-Promoted Sandmeyer Difluoromethylthiolation of Aryl and Heteroaryl Diazonium Salts” Angew. Chem. Int. Ed. 2015, 54, 7648

 

7.       Xu, C.-F.; Ma, B.-Q.; Shen, Q.* “N-Trifluoromethylthiosaccharin: An Easily Accessible, Shelf-Stable, Broadly Applicable Trifluoromethylthiolating Reagent”  Angew. Chem. Int. Ed. 2014, 53, 9316

 

8.       Hu, F.; Shao, X.-X.; Zu, D.-H.; Lu, L.; Shen, Q.* “Silver-Catalyzed Decarboxylative Trifluoromethylthiolation of Aliphatic Carboxylic Acids in Aqueous Emulsion” Angew. Chem. Int. Ed. 2014, 53, 6105.

 

9.       Wang, X.-Q.; Yang, T.; Cheng, X.-L.; Shen, Q.* “Enantioselective Electrophilic Trifluoromethylthiolation of b-Ketoesters: A Case of Reactivity and Selectivity Bias for Organocatalysis” Angew. Chem. Int. Ed. 2013, 52, 12860

 

10.    Shao, X.-X.; Wang, X.-Q.; Yang, T.; Lu, L.*; Shen, Q.* “An Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation” Angew. Chem. Int. Ed. 2013, 52, 3457

 

11.    Liu, T.; Shao, X.-X.; Wu, Y.-M.; Shen, Q.* “Highly Selective Trifluoromethylation of 1,3-Disubstituted Arenes through Iridium-Catalyzed Arene Borylation” Angew. Chem. Int. Ed. 2012, 51, 540.

 

12.    Xu, C.-F.; Shen, Q.*Lewis Acid Mediated Trifluoromethylthio Lactonization/Lactamization” Org. Lett. 2015, 17, 4561

 

13.    Liu, Y.-F.; Shao, X.-X.; Lu, L.*; Shen, Q.*Trifluoromethyl-Substituted Sulfonium Ylide: Rh-Catalyzed Carbenoid Addition to Trifluoromethylthioether” Org. Lett. 2015, 17, 2752

 

14.    Xu, C.-F.; Shen, Q.* “Palladium-Catalyzed Trifluoromethylthiolation of Aryl C−H Bonds” Org. Lett. 2014, 16, 2046

 

15.    Yu, D.-H.; Wang, C.-S.; Yao, C.; Shen, Q.;* Lu, L.* “Nickel-Catalyzed α-Arylation of Zinc Enolates with Polyfluoroarenes via C–F Bond Activation under Neutral Conditions” Org. Lett. 2014, 16, 5544.

 

16.    Shao, X.-X.; Liu, T.-F.; Lu, L.;* Shen, Q.* “Copper-Catalyzed Trifluoromethyl-thiolation of Primary and Secondary Alkylboronic Acids” Org. Lett. 2014, 16, 4738

 

17.    Yu, D.-H.; Lu, L.;* Shen, Q.* “Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C_F/C_H Activation” Org. Lett. 2013, 15, 940

 

18.    Liu, T.; Shen, Q.* “Copper-Catalyzed Trifluoromethylation of Aryl and Vinyl Boronic Acids with An Electrophilic Trifluoromethylating Reagent” Org. Lett. 2011, 13, 2342.

 

19.    Wen, L.; Shen, Q.; Lu, L.* “Enantioselective Organocatalytic Michael Addition of Aldehydes to Trifluoroethylidene Malonates” Org. Lett. 2010, 12, 4655.

 

20.    Shao, X.-X.; Xu, C.-F.; Lu, L.;* Shen, Q.* “Structure−Reactivity Relationship of Trifluoromethanesulfenates: Discovery of an Electrophilic Trifluoromethylthiolating Reagent” J. Org. Chem. 2015, 80, 3012

 

21.    Hu, Z.-J.; Li, Y.-G.; Liu, K.; Shen, Q.* “Bis(perfluoroalkyl) Phosphino-Oxazoline: A Modular, Stable, Strongly π-Accepting Ligand for Asymmetric Catalysis” J. Org. Chem. 2012, 77, 7957

 

22.    Xu, C.-F.; Chen, S.; Lu, L.;* Shen Q.* “Preparation of Trifluorostyrenes via Palladium-Catalyzed Coupling of Aryl Boronic Acids with Chloro- and Bromo-Trifluoroethylene” J. Org. Chem. 2012, 77, 10314.

 

23.    Yu, D.-H.; Shen, Q.;* Lu, L.* “Selective Palladium-Catalyzed C−F Activation/Carbon−Carbon Bond Formation of Polyfluoroaryl Oxazolines”, J. Org. Chem. 2012, 77, 1798.

 

24.    Kang, K.; Xu, C.-F.; Shen Q.* “Copper-catalyzed Trifluoromethylthiolation of Aryl and Vinyl Boronic Acids with a Shelf-Stable Electrophilic Trifluoromethylthiolating Reagent” Org. Chem. Front. 2014, 1, 294.

 

25.    Yang, T.; Long Lu, L.;* Shen Q.*Iron-mediated Markovnikov-selective hydro-trifluoromethylthiolation of unactivated alkenes” Chem. Commun. 2015, 51, 5479.

 

26.    Chang, D.-L.; Gu, Y.; Shen Q.* “Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates and Nonaflates” Chem. Eur. J. 2015, 2015, 21, 6074

 

27.    Wen, L.-L.; Yin, L.; Shen, Q.;* Lu, L.* “Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides” ACS Catal. 2013, 3, 502

 

28.    Gu, Y.; Chang, D.-L.; Leng, X.-B.; Gu, Y.-C.; Shen Q.* “Well-Defined, Shelf-Stable (NHC)Ag(CF2H) Complexes for Difluoromethylation” Organometallics 2015, 34, 3065

 

29.    Lin, H.; Dong, X.-C.; Li, Y.-X.;* Shen, Q.;* Lu, L.* “Highly Selective Activation of Vinyl C-S Bond over Aryl C-S Bond in Pd-Catalyzed Coupling of Trifluoromethyl-ated Vinyl Diphenyl Sulfonium Salts. A General Protocol to Trifluoromethylated Alkenes and Dienes” Eur. J. Org. Chem. 2012, 4675

 

30.    Liu, T.-F.; Shen, Q.* “Progresses in Copper-mediated Formation of Trifluoromethylated Arene” Eur. J. Org. Chem. 2012, 6679

 

31.    Ma, B.-Q.; Shao, X.-X.; Shen, Q.* “BrØsted Acid-Catalyzed Electrophilic Trifluoromethylthiolation of Indoles Using Thermally Stable Trifluoromethylthiolating Reagent” J. Fluorine Chem. 2015, 171, 73.

 

32.    Yang, T.; Shen, Q.;* Lu, L.* Chincona Alkaloid-Catalyzed Enantioselective Trifluoromethylthiolation of Oxindoles” Chin. J. Chem. 2014, 32, 678.

 

33.    Chen, S.; Xu, C.-F.; Lu, L.;* Shen, Q.* “Palladium-Catalyzed Cross-Coupling of Fluorinated Vinyl Chlorides with Terminal Alkynes: A General Protocol to Fluorinated Enynes” Chin. J. Chem. 2013, 31, 901

 

34.    Lu, C.-P.; Shen, Q.; Liu, D.* “Transition Metal-Catalyzed Arene Trifluoromethylation” Youji Huaxue 2012, 32, 1380-1387.

 

35.    Liu, T.; Shen, Q.* “Copper-Catalyzed Trifluoromethylation of Aryl and Vinyl Boronic Acids with An Electrophilic Trifluoromethylating Reagent” Org. Lett. 2011, 13, 2342

 

36.    Lin, H.; Shen, Q.; Lu, L. “(β-Trifluoromethyl)Vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds” J. Org. Chem. 2011, 76, 7359

 

37.    Wen, L.; Shen, Q.; Wan, X.; Lu, L. “Enantioselective Friedel-Crafts Alkylation of Indoles with Trifluoroethylidene Malonates by Copper-Bis(Oxazoline) Complexes: Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Center” J. Org. Chem. 2011, 76, 2282

 

38.    Zhang, H.; Shen, Q.; Lu, L. “Highly Diastereoselective Synthesis of Optically Pure Trifluoromethyl-Substituted Imidazolidine, Oxazolidine and Thiazolidine” Tetrahedron Lett. 2011, 52, 349

 

39.    Wen, L.; Shen, Q.;  Lu, L. “The Recent Development of Organofluorine Chemistry in China: Asymmetric Construction of Stereogenic Trifluoromethyl-Substituted Carbon Center” Chimia 2011, 65, 894

 

40.    Qi, Q.; Shen, Q.; Lu, L. “Polyfluoroalkylation of 2-Aminothiazoles: Unexpected sp3 C-Cl Substitution Under Mild Conditions” Chinese J. Chem. 2011, 29, 2681

 

41.    Cruso, M. M.; Davis, D. A.; Shen, Q.; Odom, S. A.; Sottos, N. R.;* White, S. W.;* Moore, J. F.* “Mechanically-Induced Chemical Changes in Polymeric Materials” Chem. Rev. 2009, 109, 5755-5798.

 

42.    Shen, Q.; Hartwig, J. F.* “[(CyPF-tBu)PdCl2]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides” Org. Lett. 2008, 10, 4109-4112.

 

43.    Shen, Q.; Ogata, T.; Hartwig, J. F.* “Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity Relationships” J. Am. Chem. Soc. 2008, 130, 6586-6596. (This paper was highlighted in Synfacts, 2008, 8, 859 as synfact of the month.)

 

44.    Shen, Q.; Hartwig, J. F.* “Lewis Acid Acceleration of C-N Bond-Forming Reductive Elimination from Heteroaryl Palladium Complexes and Catalytic Amidation of Heteroaryl Bromides” J. Am. Chem. Soc. 2007, 129, 7734-7735.

 

45.    Shen, Q.; Hartwig, J. F.* “Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides” J. Am. Chem. Soc. 2006, 128, 10028-10029. (This publication was listed as one of the most-accessed communications in J. Am. Chem. Soc. for the July-September 2006 period. This paper was also featured in C&E News, 2006, 84, 32. In addition, this paper was highlighted in Angew. Chem. Int. Ed. 2007, 46, 3402-3404.)

 

46.    Fernández-Rodríguez, M. A.; Shen, Q.; and Hartwig, J. F.* “Highly Efficient and Functional-Group-Tolerant Catalysts for the Palladium-Catalyzed Coupling of Aryl Chlorides with Thiols” Chem. Eur. J. 2006, 12, 7582-7596.

 

47.    Fernández-Rodríguez, M. A.; Shen, Q.; and Hartwig, J. F.* “A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols” J. Am. Chem. Soc. 2006, 128, 2180-2181.

 

48.    Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F.* “Highly Reactive, General, and Long-Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles”, Angew. Chem. Int. Ed. 2005, 44, 1371-1375.

 

49.    Shen Q.; Hammond, G. B.* “Regiospecific Synthesis of Bicyclo- and Heterobicyclo- gem-Difluorocyclobutenes Using Functionalized Fluoroallenes and a Novel Mo-Catalyzed Intramolecular [2 + 2] Cycloaddition Reaction” J. Am. Chem. Soc. 2002, 124, 6534-6535.

 

50.    Shen, Q.; Chen, C.; Hammond, G. B.* “Synthesis and X-ray Information of Substituted gem-Difluoroallenyl Amines”, J. Fluorine Chem. 2002, 117, 131-135.

 

51.    Shen Q.; Hammond, G. B.* “Highly Efficient Synthesis of 1,1-Difluoro -2-substituted-1, 3-dienes and Dienynes from gem-Difluorohomoallenyl Bromide via Palladium-Catalyzed Cross-Coupling Reaction”, Org. Lett. 2001, 3, 2213-2215.


Students

已指导学生

刘凯  硕士研究生  070303-有机化学  

马冰清  硕士研究生  070303-有机化学  

刘天飞  博士研究生  070303-有机化学  

李玉光  博士研究生  070303-有机化学  

胡宗剑  博士研究生  070303-有机化学  

常大路  硕士研究生  070303-有机化学  

徐春发  博士研究生  070303-有机化学  

古阳  博士研究生  070303-有机化学  

康凯  博士研究生  070303-有机化学  

现指导学生

朱建生  博士研究生  070303-有机化学  

吴江  博士研究生  070303-有机化学  

路则海  博士研究生  070303-有机化学  

刘贺  硕士研究生  070303-有机化学  

肖旖飒  硕士研究生  070303-有机化学  

吕昌辉  博士研究生  070303-有机化学  

张赫  博士研究生  070303-有机化学  

王广宇  硕士研究生  070303-有机化学  

徐松松  硕士研究生  070303-有机化学  

葛航铭  博士研究生  070303-有机化学  

黄伟臣  博士研究生  070303-有机化学