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成果及论文



Independent Work

2024

48. "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. 2024xx, 10.1021/jacs.4c01506. 


Abstract Image


47. Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis

Fan, Y.; Huang, Z.; Lu, Y. Zhu, S.;* Chu, L.*. Angew. Chem. Int. Ed. 2024, 63(5), e202315974.


Description unavailable



2023

46. " Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer"

Qin, J.; Zhang, Z.; Lu, Y. Zhu, S.; Chu, L.*. Chem. Sci. 2023,14, 12143-12151.

Graphical abstract: Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer


45.“Visible-light-induced defluorinative allylation of difluoromethyl ketones using alkylamines as bifunctional agents.”

Jiao, X.; Huang, Z.; MengW.Zhu, S.*;  Chu, L.*.Org. Chem. Front. 202310, 4542-4549.

# 2023 Organic Chemistry Frontiers HOT articles



44. "Nickel-Catalyzed Markovnikov-Selective Hydrodifluoromethylation of Alkynes Using BrCF2H."

Pan, S.; Chen, F.; Zhang, Y.; Shao, L.;Chu, L.*. Angew. Chem. Int. Ed. 2023, 62(31), e202305426.


Description unavailable


43."Site- and Stereoselective Synthesis of Alkenyl Chlorides by Dual Functionalization of Internal Alkynes via Photoredox/Nickel Catalysis."


Huo, L.; Li, X,; Zhao, Y.; Li, L.; Chu, L.*. J. Am. Chem. Soc. 2023, 145 (17), 9876–9885. 



42. "Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions."


Zhang, Y.; Zhang, Z.; Zhu, S*.; Chu, L.*. Chin. J. Org. Chem202343(3), 1023-1035.


# Invited review



41. "Ligand-controlled stereodivergent alkenylation of alkynes to access functionalized trans- and cis-1,3-dienes"


Long, T.;# Zhu, C.;# Li, L.; Shao, L.; Zhu, S.; Rueping, M.;*Chu, L.* Nat. Commun. 202314, 55.



40. "Exploring visible light for carbon–nitrogen and carbon–oxygen bond formation via nickel catalysis"

Zhu, S.;Li, H.; Li, Y.; Huang, Z.; Chu, L.* Org. Chem. Front. 2023, 10, 548-569.

Themed collection: Frontiers Emerging Investigators Series


Graphical abstract: Exploring visible light for carbon–nitrogen and carbon–oxygen bond formation via nickel catalysis


39. "Three-component enantioselective alkenylation of organophosphonates via nickel metallaphotoredox catalysis

Li, X.;# Yuan, M.;# Chen, F.; Huang, Z.; Qing, F.-L.; Gutierrez, O.;* Chu, L.* Chem, 2023, 9(1), 154-169.



2022

38. "Light-Induced Divergent Cyanation of Alkynes Enabled by Phosphorus Radicals"

Zhang, Y.; Han, Y.; Zhu, S.;* Qing, F.-L.; Xue, X.-S.* Chu, L.*Angew. Chem. Int. Ed. 2022, 61(50), e202210838.



37. "Selective Three-Component Reductive Alkylalkenylation of Unbiased Alkenes via Carbonyl-Directed Nickel Catalysis"

Wang, F.; Pan, S.; Zhu, S.; Chu, L.* ACS Catal. 2022, 12, 9779–9789.


Abstract Image


36. "Photoredox-catalyst-controlled divergent alkylation of α-CF3-olefins"

Chen, F. Chu, L.* Chem. Catal. 20222, 1247-1249

# Invited Preview



35. "Metallaphotoredox-Enabled Intermolecular Carbobromination of Alkynes with Alkenyl Bromides"

Yu, W.; Jiao, X.; Fan, Y.; Zhu, S.;* Chu, L.*  Adv. Synth. Catal. 2022, 364, 1239-1244.


34. "Catalyst-Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible-Light-Induced Charge Transfer"

Long, T.; Pan, S.; Zhu, S.; Chu, L.Chem. Eur. J. 2022, 28, e202104080


Description unavailable


33. "Selective Fluoromethyl Couplings of Alkynes via Nickel Catalysis"

Li, H.; Wang, F.; Zhu, S.; Chu, L.*  Angew. Chem. Int. Ed. 2022, 61, e202116725.


Description unavailable



32. "Selective Ni-catalyzed cross-electrophile coupling of alkynes, fluoroalkyl halides, and vinyl halides
Dai, Y.; Wang, F.; Zhu, S.; Chu, L.Chin. Chem. Lett. 2022, 33, 4074-4078.

 # Special issue for "Fluorine Chemistry"


2021

31. "Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis"
Zhao, X.; Feng, X.; Chen, F.; Zhu, S.; Qing, F.-L.; Chu, L.* Angew. Chem. Int. Ed. 2021, 60 (51), 26511-26517.

Description unavailable


30. "Recent Advances in Photoredox/Nickel Dual-Catalyzed Difunctionalization of Alkenes and Alkynes
Xu, L.; Wang, F.; Chen, F.; Zhu, S.; Chu, L.* Chin. J. Org. Chem. 2021, 41, DOI: 10.6023/cjoc202109002.

# Invited review


29. "Catalytic three-component dicarbofunctionalization reactions involving radical capture by nickel

Zhu, S,-Q.; Zhao, X.; Li, H.; Chu, L.* Chem. Soc. Rev. 2021, 50, 10836-10856.

# This article is part of the themed collection: Radical Chemistry

Graphical abstract: Catalytic three-component dicarbofunctionalization reactions involving radical capture by nickel


28. "Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes
Li, X.; Chu, L.* Chin. J. Org. Chem. 2021, 41, 410-4102.

# Invited Highlight


27. "Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis”
Zhao, X.; Zhu, S,-Q.; Qing, F.-L.; Chu, L.* Chem. Commun.  2021, 57, 9414-9417.

# This article is part of the themed collection: 2021 Emerging Investigators


Graphical abstract:Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis


26. "Radical 1,2-addition of bromoarenes to alkynes via dual photoredox and nickel catalysis”
Xu, L.; Zhu, S,-Q.; Huo, L,-P.; Chen, F.; Yu, W.; Chu, L.* Org. Chem. Front. 2021, 8, 2924-2931.


Graphical abstract:Radical 1,2-addition of bromoarenes to alkynes via dual photoredox and nickel catalysis


25. “Photoinduced triiodide-mediated [3+2] cycloaddition of N-tosyl aziridines and alkenes”
Li, Y.; Chen, F.; Zhu, S.; Chu, L.* Org. Chem. Front. 2021, 8, 2196-2202.


Graphical abstract:Photoinduced triiodide-mediated [3 + 2] cycloaddition of N-tosyl aziridines and alkenes


24. "Dual Photoredox-/Palladium-Catalyzed Cross-Electrophile Couplings of Polyfluoroarenes with Aryl Halides and Triflates"

Qin, J.; Zhu, S.; Chu, L.* Organometallics 2021, 40, 2246-2252.

This article is part of the "Organometallic Solutions to Challenges in Cross-Coupling" special issue.



23. "Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis"
Feng, X.; Guo, L.; Zhu, S.; Chu, L.* Synlett 2021, 32, 1519-1524.

# cluster "Modern Nickel-Catalyzed Reactions"



22. "Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF2H"
Yang, J.#; Zhu, S.#; Wang, F.; Qing, F.-L.; Chu, L.* Angew. Chem. Int. Ed. 2021, 60, 4300-4306.


image


21. "Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes"
Wang, F.; Qin, J.; Zhu, S.; Chu, L.RSC Adv. 202111, 142-146.


Graphical abstract: Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes


2020
20. "Cu-Catalyzed Regio-and Stereo-selective 1,3-and 1,4-Diborylations of CF3-Containing 1,3-Enynes"
Zhu, S.; Chu, L.* Chin. J. Org. Chem. 2020, 40, 3980-3981.

Invited Highlight


19. "General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis"
Guo, L.#; Yuan, M.#; Zhang, Y.; Wang, F.; Zhu, S.; Osvaldo Gutierrez*; Chu, L.* J. Am. Chem. Soc. 2020, 142, 20390-20399.



18. "Synergistic Catalysis for Stereodivergent Synthesis of trans- and cis-Skipped Dienes"
Wang, F.; Zhu, S.*; Chu, L.* Synlett 2020, 31, 1741-1746.

Invited Synpact


17. "Enantioselective Three-Component Fluoroalkylarylation of UnactivatedOlefins Through Nickel-Catalyzed Cross-Electrophile Coupling"
Tu, H.#; Wang, F.#; Huo, L.; Li, Y.; Zhu, S.; Zhao, X.; Li, H.; Qing, F.-L.; Chu, L.* J. Am. Chem. Soc. 2020, 142, 9604-9611.


Abstract Image


16. "Sequential C-O Decarboxylative Vinylation/C-H Arylation of Cyclic Oxalates via Nickel-Catalyzed Multicomponent Radical Cascade"
Li, H.#; Guo, L.#; Feng, X.; Huo, L.; Zhu, S.; Chu, L.* Chem. Sci. 2020, 11, 4904-4910.


Graphical abstract:Sequential C–O decarboxylative vinylation/C–H arylation of cyclic oxalates via a nickel-catalyzed multicomponent radical cascade


15. "Recent advances in photoredox and nickel dual-catalyzed cascade reactions: pushing the boundaries of complexity"
Zhu, C.; Yue, H.-F.; Chu, L.; Rueping, M. Chem. Sci. 2020, 11, 4051-4064.

Invited review

Graphical abstract:Recent advances in photoredox and nickel dual-catalyzed cascade reactions:pushing the boundaries of complexity


14. "Recent Advances in Nickel-Catalyzed Three-Component Difunctionalization of Unactivated Alkenes"
Tu, H.-Y.; Zhu, S.*; Qing, F.-L.; Chu, L.* Synthesis 2020, 52, 1346-1356.

Invited review


2019

13. "Visible‐Light‐Enabled Stereodivergent Synthesis of (E)‐ and (Z)‐1,4‐Dienes via Photoredox/Nickel Dual Catalysis"
Song, F.#; Wang, F.#; Guo, L.; Feng, X.; Zhang, Y.; Chu, L.* Angew. Chem. Int. Ed. 2019, 59, 177-181.

# Hot paper

image


12. "Bisphosphonium salt: an effective photocatalyst for the intramolecular hydroalkoxylation of olefins"
Cheng, H.; Wang, X.; Chang, L.; Chen, Y.-L.; Chu, L.*; Zuo, Z.-W.* Sci. Bull. 2019, 64, 1896-1901.



11. "Selective, Intermolecular Alkylarylation of Alkenes via Photoredox/Nickel Dual Catalysis"
Guo, L.#; Tu, H.-Y.#; Zhu, S.-Q.; Chu, L.* Org. Lett. 2019, 21, 4771-4776.


Abstract Image


10. "Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine"
Zhu, S.; Qin, J.; Wang, F.; Li, H.; Chu, L.* Nat. Commun. 2019, 10, 749.



9. "Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis"
Chen, J.#; Zhu, S.#; Qin, J.; Chu, L.* Chem. Commun. 2019, 55, 2336-2339.



2018
8. "Solvent-tuned chemoselective carboazidation and diazidation of alkenes via iron catalysis"
Xu, L.; Chen, J.; Chu, L.* Org. Chem. Front. 2018, 6, 512-516.


Graphical abstract: Solvent-tuned chemoselective carboazidation and diazidation of alkenes via iron catalysis


7. “A four-component radical cascade trifluoromethylation reaction of alkenes enabled by an electron-donor–acceptor complex”
Tu, H.-Y.; Zhu, S.; Qing, F.-L.; Chu, L.* Chem. Commun. 2018, 54, 12710-12713.


Graphical abstract: A four-component radical cascade trifluoromethylation reaction of alkenes enabled by an electron-donor–acceptor complex


6. "Metal-free, intermolecular carbopyridylation of alkenes via visible-light-induced reductive radical coupling"
Chen, D.; Xu, L.; Long, T.; Zhu, S.; Yang, J.; Chu, L.* Chem. Sci. 2018, 9, 9012-9017.


Graphical abstract: Metal-free, intermolecular carbopyridylation of alkenes via visible-light-induced reductive radical coupling


5. "syn-Selective Alkylarylation of Terminal Alkynes via the Combination of Photoredox and Nickel Catalysis"
Guo, L.; Song, F.; Zhu, S.; Li, H.; Chu, L.* Nat. Commun. 2018, 9, 4543.



4. "Ligand-Accelerated, Branch-Selective Oxidative Cyanation of Alkenes"
Yang, J.; Li, H.; Qin, J.; Song, F.; Zhang, J.; Qing, F.-L.; Chu, L.* Sci. Bull. 2018, 63, 1479-1484.



3. "Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay"
Zhao, X.#; Tu, H.-Y.#; Guo, L.; Zhu, S.; Qing F.-L.; Chu, L.* Nat. Commun. 2018, 9, 3488.



2. "Catalytic, Metal-free Sulfonylcyanation of Alkenes via Visible Light Organophotoredox Catalysis"
Sun, J.#; Li, P.#; Guo, L.; Yu, F.; He, Y.-P.*; Chu, L.* Chem. Commun. 2018, 54, 3162-3165.



2017
1. "Visible-light-induced Halogenation of Aliphatic C-H Bonds"
Tu, H.; Zhu, S.; Qing, F.-L.; Chu, L.* Tetrahedron Lett. 2017, 59, 173-179
.

Invited review


Prior to DHU

24. "Silver-Mediated Oxidative Trifluoromethylation of Phenols: Direct Synthesis of Aryl Trifluoromethyl Ethers"
Liu, J.-B.; Chen, C.; Chu, L.; Chen, Z.-H.; Xu, X.-H.; Qing, F.-L.* Angew. Chem. Int. Ed. 2015, 54, 11839-11842.

23. "Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones via the Decarboxylative Arylation of α-Oxo Acids"
Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C.* Angew. Chem. Int. Ed. 2015, 54, 7929−7933 (Very Important Paper).

22. "Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin"
Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C.* J. Am. Chem. Soc. 2014, 136, 10886−10889.

21. "Merging Photoredox with Nickel Catalysis: Coupling of α-Carboxyl sp3-Carbons with Aryl Halides"
Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.*; MacMillan, D.W. C.* Science 2014, 345, 437−440.

20. "Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as A Nucleophilic CF3 Source"
Chu, L.; Qing, F.-L.* Acc. Chem. Res. 2014, 47, 1513−1522.

19. "Direct introduction of ethoxycarbonyldifluoromethyl-group to heteroarenes with ethyl bromodifluoroacetate via visible-light photocatalysis"
Lin, Q.; Chu, L.; Qing, F.-L.* Chin. J. Chem. 2013, 31, 885-891.

18. "Copper-Mediated Oxidative Difluoromethylenation of Aryl Boronic Acids with a-Silyldifluoromethylphosphonates: A New Method for Aryldifluorophosphonates"
Jiang, X.; Chu, L.; Qing, F.-L.* New J. Chem. 2013, 37, 1736−1741.

17. "Total Synthesis of the Trifluoromethylated Analog of Isoaltholactone: 5-Trifluoromethylisoaltholactone"
Chen, J.-L.; Chu, L.; Qing, F.-L.* J. Fluorine Chem. 2013, 152, 70−76.

16. "Electrophilic Trifluoromethylthiolation of Allylsilanes with Trifluoromethanesulfanamide"
Liu, J.; Chu, L.; Qing, F.-L.* Org. Lett. 2013, 15, 894−897.

15. "Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3"
Wu, X.; Chu, L.; Qing, F.-L.* Angew. Chem. Int. Ed. 2013, 52, 2198−2202.

14. "PhI(OAc)2-mediated Oxidative Trifluoromethylation of Arenes with CF3SiMe3 under Metal-free Conditions"
Wu, X.; Chu, L.; Qing, F.-L.* Tetrahedron Lett. 2013, 54, 249−251.

13. "Synthesis of γ-Fluoroalkylated Allylic Amines Derivatives via Palladium-catalyzed Overman Rearrangement"
Jiang, X.-Y.; Chu, L.; Wang, R.-W.; Qing, F.-L.* Tetrahedron Lett. 2012, 53, 6853−6857.

12. "Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur"
Chen, C.; Chu, L.; Qing, F.-L.* J. Am. Chem. Soc. 2012, 134, 12454−12457.

11. "Copper-Mediated Oxidative Cross-Coupling Reaction of Terminal Alkynes with α-Silyldifluoromethylphosphonates: An Efficient Method for α,α-Difluoropropargylphosphonates"
Jiang, X.; Chu, L.; Qing, F.-L.* Org. Lett. 2012, 14, 2870−2873.

10. "Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)–CF3 Bond Formation"
Chu, L.; Qing, F.-L.* Org. Lett. 2012, 14, 2106−2109.

9. "Copper-Catalyzed Aerobic Oxidative Trifluoromethylation of H-Phosphonates Using Trimethyl(trifluoromethyl)silane"
Chu, L.; Qing, F.-L.* Synthesis 2012, 44, 1521−1525.

8. "Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkynes and Aryl Boronic Acids Using (Trifluoromethyl)trimethylsilane"
Jiang, X.; Chu, L.; Qing, F.-L.* J. Org. Chem. 2012, 77, 1251−1257.

7. "Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur"
Chen, C.; Xie, Y.; Chu, L.; Wang, R. Zhang, X. Qing, F.-L.* Angew. Chem. Int. Ed. 2012, 51, 2492−2495.

6. "Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes"
Chu, L.; Qing, F.-L.* J. Am. Chem. Soc. 2012, 134, 1298−1304.

5. "Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids"
Chu, L.; Qing, F.-L.* Org. Lett. 2010, 12, 5060–5063.

4. "Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3"
Chu, L.; Qing, F.-L.* J. Am. Chem. Soc. 2010, 132, 7262−7263.

3. "Benzoyl Peroxide (BPO)-promoted Oxidative Trifluoromethylation of Tertiary Amines with Trimethyl(trifluoromethyl)silane"
Chu, L.; Qing, F.-L.* Chem. Commun. 2010, 46, 6285−6287.

2. "Cu(II)-Mediated Methylthiolation of Aryl C−H Bonds with DMSO"
Chu, L.; Yue, X.; Qing, F.-L.* Org. Lett. 2010, 12, 1644−1647.

1. "CuBr-Catalyzed Oxidative Difluoromethylation of Tertiary Amines with Difluoroenol Silyl Ethers"
Chu, L.; Zhang, X.; Qing, F.-L.* Org. Lett. 2009, 11, 2197−2200.