2024

1. Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl-Oxindoles. Jingrui He, Haibo Mei, Jorge Escorihuela,* Jianlin Han.* Chin. J. Chem. 2024, 42, 1691−1698. https://doi.org/10.1002/cjoc.202400127

2. Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters. Youlong Du, Haibo Mei,* Ata Makarem, Ramin Javahershenas, Vadim A. Soloshonok, Jianlin Han.* Beilstein J. Org. Chem. 2024, 20, 212–219. https://doi.org/10.3762/bjoc.20.21

3. Visible-light-promoted cyclization of 3-indolylallylamides enabling synthesis of tetrahydrocarbolinones. Jingrui He, Chengting Wang, Haibo Mei,* Ata Makarem,* Vadim A. Soloshonok, Jianlin Han.* Tetrahedron 2024, 150, 133776. https://doi.org/10.1016/j.tet.2023.133776

4. Aza-Wittig reaction of (β-diazo-α,α-difluoroethyl)phosphonates with aldehydes for the synthesis of difluoromethylphosphonate-containing arylidene hydrazones. Qian Wang, Romana Pajkert,* Haibo Mei, Gerd-Volker Roschenthaler,* Jianlin Han.* J. Fluorine Chem. 2024, 273, 110226. https://doi.org/10.1016/j.jfluchem.2023.110226

5. Visible-Light-Triggered Difluoroacetylation/Cyclization of Chromone-Tethered Alkenes Enabling Synthesis of Tetrahydroxanthones. Chengting Wang, Jingrui He, Haibo Mei,* Ata Makarem, Jianlin Han.* J. Org. Chem. 2024, 89, 5619−5633. https://doi.org/10.1021/acs.joc.4c00129

6. Synthesis of N-sulfenylimines via an electrochemical radical coupling of amines and thiols mediated by bromide ions. Qian Wang, Haibo Mei,* Romana Pajkert, Gerd-Volker Röschenthaler,* Jianlin Han.* Tetrahedron 2024, 162, 134133. https://doi.org/10.1016/j.tet.2024.134133

7. FDA approved fluorine-containing drugs in 2023. Qian Wang, Yeping Bian,* Gagan Dhawan,* Wei Zhang,* Alexander E. Sorochinsky,* Ata Makarem, Vadim A. Soloshonok,* Jianlin Han.* Chin. Chem. Lett. 2024, 35, 109780. https://doi.org/10.1016/j.cclet.2024.109780

8. Cu-Catalyzed Reaction of Trifluoromethylated β-Keto Diazos and Nitriles Proceeding via H₂O Addition to Nitrile Ylides. Haibo Mei,* Youlong Du, Qian Wang, Jorge Escorihuela,* Loránd Kiss,* Vadim A. Soloshonok,* Jianlin Han.* Adv. Synth. Catal. 2024, 366, 3443 – 3449. https://doi.org/10.1002/adsc.202400402

9. Recent Advances on the Synthesis and Application of Tetrahydro β-Carbolines. Youlong Du, Anas Semghouli, Haibo Mei,* Loránd Kiss,*  Jianlin Han.*  Adv. Synth. Catal. 2024, 366, 3050–3084. https://doi.org/10.1002/adsc.202400306

10. Recent Advances on the Synthesis and Application of α,α-Difluoro-β-aminophosphonates. Youlong Du, Qian Wang, Haibo Mei,*  Romana Pajkert,* Gerd-Volker Röschen thaler,* Jianlin Han.* Chin. J. Org. Chem. 2024, 44(x), xxxx doi: 10.6023/cjoc202405013.

2023

1. Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles. Jingrui He, Aiyao Liu, Yingjie Yu, Chengting Wang, Haibo Mei,* Jianlin Han.* J. Org. Chem. 2023, 88, 6962−6972. https://doi.org/10.1021/acs.joc.3c00267

2. A Cu-promoted reaction of β-keto trifluoromethyl amines enabling stereoselective synthesis of trifluoromethylated aziridines. Nana Wang, Youlong Du, Haibo Mei,* Jorge Escorihuela, Jianlin Han.* Org. Biomol. Chem. 2023, 21, 4988–4992. https://doi.org/10.1039/D3OB00714F

3. Electrochemical reaction of indole-tethered alkynes enabling stereoselective construction of tetrahydro-γ-carbolines. Chengting Wang, Jingrui He, Haibo Mei,* Jianlin Han.* Tetrahedron Lett. 2023, 127, 154664. https://doi.org/10.1016/j.tetlet.2023.154664

4. A three-component cycloaddition of alkyl trifluorodiazoethane for the synthesis of trifluoromethylated isoxazolines. Jingcheng Xu, Jiang Liu, Haibo Mei,* Vadim A. Soloshonok,* Jianlin Han.* Chemistry of Heterocyclic Compounds 2023, 59, 465–471. https://doi.org/10.1007/s10593-023-03217-8

5. Cascade Detrifluoroacetylation, C-S Bond Cleavage, and S_N2′ Reaction of α,α-Difluorinated Gem-Diols with MBH Esters. Xinyu Yao, Ziyi Li, Haibo Mei,* Jorge Escorihuela,* Vadim A. Soloshonok, Jianlin Han.* J. Org. Chem. 2023, 88, 13057−13066. https://doi.org/10.1021/acs.joc.3c01220

6. Recent advances on the synthesis and application of tetrahydro- γ-carbolines. Haibo Mei, Klára Aradi, Loránd Kiss,* Jianlin Han.* Chin. Chem. Lett. 2023, 34, 108657. https://doi.org/10.1016/j.cclet.2023.108657

7. Fluorine-containing drugs approved by the FDA in 2021. Jingrui He, Ziyi Li, Gagan Dhawan,* Wei Zhang,* Alexander E. Sorochinsky, Greg Butler, Vadim A. Soloshonok,* Jianlin Han.* Chin. Chem. Lett. 2023, 34, 107578. https://doi.org/10.1016/j.cclet.2022.06.001

8. Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies. Ziyi Li, Hua Gao, Haibo Mei, Guangwei Wu,* Vadim A. Soloshonok, Jianlin Han.* Molecules 2023, 28, 4067.  https://doi.org/10.3390/molecules28104067

9. New Approved Drugs Appearing in the Pharmaceutical Market in 2022 Featuring Fragments of Tailor-Made Amino Acids and Fluorine. Nana Wang, Haibo Mei, Gagan Dhawan,* Wei Zhang,* Jianlin Han,* Vadim A. Soloshonok.* Molecules 2023, 28, 3651. https://doi.org/10.3390/molecules28093651

10. Rh-Catalyzed Hydration/C􀀀 F Bond Cleavage of Fluorinated Diazoalkanes Enabling Synthesis of α-Fluoro-β-ketophosphonates. Qian Wang, Jiang Liu, Haibo Mei, Romana Pajkert,* Gerd-Volker Röschenthaler,* Jianlin Han.* Adv. Synth. Catal. 2023, 365, 2883– 2887.  

2022

1. Carboxylic Acid O−H Insertion Reaction of β‑Ester Diazos Enabling Synthesis of β‑Acyloxy Esters. Ziyi Li, Xinyu Yao, Xin Zhang, Haibo Mei,* Jianlin Han.* J. Org. Chem. 2022, 87, 15483−15491. https://doi.org/10.1021/acs.joc.2c02023

2. Arylsulfonylation-Triggered Cyclization of 3‑Alkenyl Indoles Enabling Synthesis of Tetrahydro-γ-carboline. Aiyao Liu, Jingrui He, Yingjie Yu, Chengting Wang, Haibo Mei,* Jianlin Han.* J. Org. Chem. 2022, 87, 11469−11477. https://doi.org/10.1021/acs.joc.2c01033

3. Facile synthesis of ( β-chlorodifluoroethyl)phosphonates via chlorination reaction of difluoroalkyl diazo derivatives with HCl. Jiang Liu, Romana Pajkert, Li Wang, Haibo Mei,* Gerd-Volker Röschenthaler,* Jianlin Han.* Chin. Chem. Lett. 2022, 33, 2429–2432. https://doi.org/10.1016/j.cclet.2021.10.066

4. Electrochemical multi-component reaction of potassium metabisulfite with alkenes and alcohols enabling synthesis of sulfonate esters. Jiang Liu, Jingcheng Xu, Haibo Mei,* Jianlin Han.* Green Chem. 2022, 24, 6113–6118. https://doi.org/10.1039/D2GC01909D

5. Assembly of trifluoromethylated fused tricyclic pyrazoles via cyclization of β-amino cyclic ketones. Nana Wang, Yiming Qiao, Youlong Du, Haibo Mei,* Jianlin Han.* Org. Biomol. Chem. 2022, 20, 7467–7471. https://doi.org/10.1039/D2OB01391F

6. Copper-catalyzed reaction of alkyl trifluoromethyl diazoalkane for the synthesis of trifluoromethyl allenes. Jingcheng Xu, Jiang Liu, Haibo Mei,* Jianlin Han.* J. Fluorine Chem. 2022, 264, 110050. https://doi.org/10.1016/j.jfluchem.2022.110050

7. Visible-light-irradiated tandem sulfonylation/cyclization of indole tethered alkenes for the synthesis of tetrahydrocarbazoles. Yingjie Yu, Aiyao Liu, Jingrui He, Chengting Wang, Haibo Mei,* Jianlin Han.* Chin. Chem. Lett. 2022, 33, 4886–4890. https://doi.org/10.1016/j.cclet.2022.03.038

8. Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines. Haibo Mei, Aiyao Liu, Jingrui He, Yingjie Yu, Jianlin Han.* Org. Lett. 2022, 24, 2630−2635. https://doi.org/10.1021/acs.orglett.2c00626

9. Intramolecular Appel Reaction of Trifluoromethylated β‑Keto Diazos Enabling Assembly of Trifluoromethylpyrazoles. Haibo Mei, Nana Wang, Ziyi Li, Jianlin Han.* Org. Lett. 2022, 24, 2258−2263. https://doi.org/10.1021/acs.orglett.2c00738

10. Assembly of tetracyclic tetrahydrocarbazoles via a visible-light promoted cascade process. Haibo Mei, Yingjie Yu, Chengting Wang, Aiyao Liu, Jianlin Han.* Org. Chem. Front. 2022, 9, 2516–2521. https://doi.org/10.1039/D2QO00247G

11. Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives. Jianlin Han, Jorge Escorihuela, Santos Fustero,* Aitor Landa, Vadim A. Soloshonok, Alexander Sorochinsky.* Molecules 2022, 27, 3797. https://doi.org/10.3390/molecules27123797

12. New pharmaceuticals approved by FDA in 2020: Smallmolecule drugs derived from amino acids and related compounds. Aiyao Liu, Jianlin Han,* Arina Nakano, Hiroyuki Konno, Hiroki Moriwaki, Hidenori Abe, Kunisuke Izawa,* Vadim A. Soloshonok.* Chirality 2022, 34, 86–103. https://doi.org/10.1002/chir.23376

13. Successful trifluoromethoxy-containing pharmaceuticals and agrochemicals. Jiang Liu, Weikang Lin, Alexander E. Sorochinsky,* Greg Butler, Aitor Landa, Jianlin Han,* Vadim A. Soloshonok .* J. Fluorine Chem. 2022, 257–258, 109978. https://doi.org/10.1016/j.jfluchem.2022.109978

14. One-Pot Reaction of (β-Amino-α,α-difluoroethyl)phosphonates with Trifluoromethylated Ketones via Aza-Wittig Reagents. Qian Wang, Jiang Liu, Nana Wang, Romana Pajkert, Haibo Mei, Gerd-Volker Röschenthaler,* Jianlin Han.* Adv. Synth. Catal. 2022, 364, 1969–1974. https://doi.org/10.1002/adsc.202200330

15. Ru-Catalyzed Hydrogen Atom Transfer/C−F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process. Qian Wang, Jiang Liu, Haibo Mei, Romana Pajkert, Mira Kessler,* Gerd-Volker Röschenthaler,* Jianlin Han.* Org. Lett. 2022, 24, 8036−8040. https://doi.org/10.1021/acs.orglett.2c03268

16. The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine.Qian Wang, Jianlin Han,* Alexander Sorochinsky,* Aitor Landa, Greg Butler, Vadim A. Soloshonok.* Pharmaceuticals 2022, 15, 999. https://doi.org/10.3390/ph15080999

2021

1. Synthesis of Isothiazoles through N‑Propargylsulfinylamide: TFAPromoted Sulfinyl Group-Involved Intramolecular Cyclization. Ziyi Li, Nana Wang, Jiang Liu, Haibo Mei,* Vadim A. Soloshonok, and Jianlin Han.* Org. Lett. 2021, 23, 6941−6945. https://doi.org/10.1021/acs.orglett.1c02538

2. [3+2] Cycloaddition reactions of β-diazo-α,α-difluoromethylphosphonates with α,β-unsaturated esters. Qian Wang, Li Wang, Romana Pajkert, Ita Hajdin, Haibo Mei,* Gerd-Volker Roschenthaler,* Jianlin Han.* J. Fluorine Chem. 2021,  251, 109899. https://doi.org/10.1016/j.jfluchem.2021.109899

3. Electrosynthesis of functionalized tetrahydrocarbazoles via sulfonylation triggered cyclization reaction of indole derivatives. Zizhen Yin, Yingjie Yu, Haibo Mei,* Jianlin Han.* Green Chem. 2021, 23, 3256–3260. https://doi.org/10.1039/D1GC00609F

4. Design of (β-diazo-α,α-difluoroethyl) phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids. Haibo Mei, Jiang Liu, Romana Pajkert, Li Wang, Gerd-Volker Röschenthaler,*  Jianlin Han.* Org. Chem. Front. 2021, 8, 767–772. https://doi.org/10.1039/D0QO01394C

5. In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3+2] Cycloaddition Reactions with Vinyl Sulfones. Haibo Mei, Li Wang, Romana Pajkert, Qian Wang, Jingcheng Xu, Jiang Liu, Gerd-Volker Röschenthaler,* Jianlin Han.* Org. Lett. 2021, 23, 1130−1134. https://doi.org/10.1021/acs.orglett.1c00150

6. A Call for a Change in Policy Regarding the Necessity for SDE Tests to Validate the Veracity of the Outcome of Enantioselective Syntheses, the Inherent Chiral State of Natural Products, and Other Cases Involving Enantioenriched Samples. Jianlin Han, Roman Dembinski, Vadim A. Soloshonok,* Karel D. Klika.* Molecules 2021, 26, 3994. https://doi.org/10.3390/molecules26133994

7. Tailor-Made Amino Acids in Pharmaceutical Industry: Synthetic Approaches to Aza-Tryptophan Derivatives. Jianlin Han,* Nataliya V. Lyutenko, Alexander E. Sorochinsky,* Ayaka Okawara, Hiroyuki Konno,* Sarah White,* Vadim A. Soloshonok.* Chem. Eur. J. 2021, 27, 17510–17528.  https://doi.org/10.1002/chem.202102485

8. Chemical Aspects of Human and Environmental Overload with Fluorine. Jianlin Han, Loránd Kiss,* Haibo Mei, Attila Márió Remete, Maja Ponikvar-Svet,* Daniel Mark Sedgwick, Raquel Roman, Santos Fustero,* Hiroki Moriwaki, Vadim A. Soloshonok.* Chem. Rev. 2021, 121, 4678−4742. https://doi.org/10.1021/acs.chemrev.0c01263

9. Peptidomimetics and Peptide-Based Blockbuster Drugs. Jianlin Han, Hiroyuki Konno, Tatsunori Sato, Kunisuke Izawa,*Vadim A. Soloshonok.* Current Org. Chem. 2021, 25, 1627-1658. https://doi.org/10.2174/1385272825666210610155047

10. Tailor-made amino acids in the design of small-molecule blockbuster drugs. Jianlin Han, Hiroyuki Konno, Tatsunori Sato, Vadim A. Soloshonok,* Kunisuke Izawa c.* Eur. J. Med. Chem. 2021, 220, 113448. https://doi.org/10.1016/j.ejmech.2021.113448

11. Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions. Jianlin Han, Alicja Wzorek, Karel D. Klika,* Vadim A. Soloshonok.* Molecules 2021, 26, 2757. https://doi.org/10.3390/molecules26092757

12. Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes. Bo Fu, Jorge Escorihuela,* Jianlin Han,* Santos Fustero,* Pablo Barrio, Mikiko Sodeoka, Shintaro Kawamura, Alexander Sorochinsky, Vadim A. Soloshonok. Molecules 2021, 26, 7221. https://doi.org/10.3390/molecules26237221

13. Asymmetric Synthesis of α-Difluorinated β-Amino Sulfones through Detrifluoroacetylative Mannich Reactions. Ziyi Li, Nana Wang, Haibo Mei, Hiroyuki Konno, Vadim A. Soloshonok, Jianlin Han.* Eur. J. Org. Chem. 2021, 3035–3038. https://doi.org/10.1002/ejoc.202100350

14. Esterification of Carboxylic Acids with (β-Diazo-α,α-difluoroethyl)phosphonates under Photochemical Conditions. Jiang Liu, Jingcheng Xu, Romana Pajkert, Haibo Mei, Gerd-Volker Röschenthaler,* Jianlin Han.* Acta Chim. Sinica 2021, 79, 747–750. DOI: 10.6023/A21030096

15. Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications. Michael Shevchuk, Qian Wang, Romana Pajkert, Jingcheng Xu, Haibo Mei, Gerd-Volker Röschenthaler,* Jianlin Han.* Adv. Synth. Catal. 2021, 363, 2912–2968. https://doi.org/10.1002/adsc.202001464

16. Electrochemical Approaches for Preparation of Tailor-Made Amino Acids. Wang, Nana, Xu, Jingcheng, Mei, Haibo, Moriwaki, Hiroki, Izawa, Kunisuke, Soloshonok, Vadim A.,* Han, Jianlin.* Chin. J. Org. Chem. 2021, 41, 3034–3049. DOI: 10.6023/cjoc202102043

17. Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity. Yingjie Yu, Aiyao Liu, Gagan Dhawan,* Haibo Mei, Wei Zhang,* Kunisuke Izawa, Vadim A. Soloshonok,* Jianlin Han.* Chin. Chem. Lett. 2021, 32, 3342–3354. https://doi.org/10.1016/j.cclet.2021.05.042

18. Asymmetric Synthesis of N-Fmoc-(S)-7-aza-tryptophan via Alkylation of Chiral Nucleophilic Glycine Equivalent. Yupiao Zou, Ryosuke Takeda, Jianlin Han,* Hiroyuki Konno, Hiroki Moriwaki, Hidenori Abe,* Kunisuke Izawa, Vadim A. Soloshonok.* Eur. J. Org. Chem. 2021, 2962–2965. https://doi.org/10.1002/ejoc.202100485

Five selected publications before 2021

1. Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C─N bond activation. Shengyang Ni, Chun-Xiao Li, Yu Mao, Jianlin Han,* Yi Wang,* Hong Yan,* Yi Pan. Sci. Adv. 2019, 5, eaaw9516. DOI: 10.1126/sciadv.aaw9516

2. Modern approaches for asymmetric construction of carbon–fluorine quaternary stereogenic centers: synthetic challenges and pharmaceutical needs. Yi Zhu, Jianlin Han,* Jiandong Wang, Norio Shibata,* Mikiko Sodeoka,* Vadim A. Soloshonok,* Jaime A. S. Coelho, and F. Dean Toste,* Chem. Rev. 2018, 118, 3887–3964. https://doi.org/10.1021/acs.chemrev.7b00778

3. Chiral sulfoxides: advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome. Jianlin Han,* Vadim A. Soloshonok,* Karel D. Klika,* Józef Drabowicz, Alicja Wzorek,* Chem. Soc. Rev. 2018, 47, 1307-1350. https://doi.org/10.1039/C6CS00703A

4. Merging Photoredox and Copper Catalysis: Enantioselective Radical Cyanoalkylation of Styrenes. Wanxing Sha, Lingling Deng, Shengyang Ni, Haibo Mei,* Jianlin Han,* Yi Pan. ACS Catal. 2018, 8, 7489−7494. https://doi.org/10.1021/acscatal.8b01863

5. Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions. Chen Xie, Lingmin Wu, Jianlin Han,* Vadim A. Soloshonok,  Yi Pan. Angew. Chem. Int. Ed. 2015, 54, 6019–6023.