One-pot dearomatizative telescoped addition of C-nucleophiles to fluorinated 1,2,4-oxadiazoles followed by regioselective N-functionalization

Davide Castiglione, Sara Amata, Federica Lauria, Andrea Maranzana, Salvatore Baldino, Alexander Prado-Roller, Laura Castoldi, Antonio Palumbo Piccionello, Vittorio Pace and Eisuke I. Comas Iwasita

Org. Chem. Front., 2026, 13, 2401
DOI: 10.1039/D5QO01707F

Hexafluoroisobutylation of enolates through a tandem elimination/allylic shift/hydrofluorination reaction

Aline Delamare, Guillaume Naulet, Brice Kauffmann, Gilles Guichard and Guillaume Compain

Chem. Sci., 2022, 13, 9507
DOI: 10.1039/D2SC02871A

Difluoromethylene cyclobutyl sulfonium salts: versatile reagents for chemodivergent synthesis of difluoroalkylated cyclobutenes and cyclobutanes

Xiao-Tian Feng, Qiao-Qiao Min, Song-Yu Zhang, Hai-Yang Zhao and Xingang Zhang

Chem. Sci., 2025, 16, 16552
DOI: 10.1039/D5SC05409E

Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF2

Margherita Miele, Laura Castoldi, Xenia Simeone, Wolfgang Holzer and Vittorio Pace

Chem. Commun., 2022, 58, 5761
DOI: 10.1039/D2CC00886F

Radical photochemical difluorosulfoximination of alkenes and propellanes

Simone Baldon, Julien Paut, Elsa Anselmi, Guillaume Dagousset, Béatrice Tuccio, Giorgio Pelosi, Sara Cuadros, Emmanuel Magnier and Luca Dell’Amico

Chem. Sci., 2025, 16, 6957
DOI: 10.1039/D5SC01068C

para-Selective dearomatization of phenols by I(i)/I(iii) catalysis-based fluorination

Timo Stünkel, Kathrin Siebold, Daichi Okumatsu, Kazuki Murata, Louise Ruyet, Constantin G. Daniliuc and Ryan Gilmour

Chem. Sci., 2023, 14, 13574
DOI: 10.1039/D3SC05952A

Geminal homologative fluorination of carbonyl derivatives en route to 1-fluoro-2-haloethyl skeletons

Margherita Miele, Davide Castiglione, Alexander Prado-Roller, Laura Castoldi and Vittorio Pace

Chem. Commun., 2025, 61, 10792
DOI: 10.1039/D5CC01542A

The rhodium riddle: computational insights into competitive β-hydride vs. β-fluoride elimination

Bijan Mirabi, Mark Lautens and Mu-Hyun Baik

Catal. Sci. Technol., 2025, 15, 2482
DOI: 10.1039/D4CY01495B

Iodonium based regioselective double nucleophilic alkene functionalization of a hydrofluoroolefin scaffold

János T. Csenki and Zoltán Novák

Chem. Commun., 2024, 60, 726
DOI: 10.1039/D3CC04985J

New conformationally flexible and recyclable aryl iodine catalysts from an inexpensive chiral source for asymmetric oxidations

Hai-Jie Zhou, Yi-Ping Yao, Tonghui Zhang, Biao Chen, Xu Wang, Hang Zhao, Jie Zeng, Jian-Ai Chen, Xiao Xiao and Fen-Er Chen

Green Chem., 2023, 25, 10447
DOI: 10.1039/D3GC02429F

Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters

Liyin Jiang, Pau Sarró, Wei Jie Teo, Jordi Llop and Marcos G. Suero

Chem. Sci., 2022, 13, 4327
DOI: 10.1039/D2SC00968D

Exploring F/CF3substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans

Anthony J. Fernandes, Bastien Michelet, Armen Panossian, Agnès Martin-Mingot, Frédéric R. Leroux and Sébastien Thibaudeau

Chem. Commun., 2023, 59, 4083
DOI: 10.1039/D2CC06521E

Catalytic Ring Expanding Difluorination: An Enantioselective Platform to Access β,β‐Difluorinated Carbocycles

Louise Ruyet, Christoph Roblick, Joel Häfliger, Zi‐Xuan Wang, Tobias Jürgen Stoffels, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2024, 136
DOI: 10.1002/ange.202403957

Skeletal Ring Contractions via I(I)/I(III) Catalysis: Stereoselective Synthesis of cis-α,α-Difluorocyclopropanes

Keith Livingstone, Kathrin Siebold, Stephanie Meyer, Víctor Martín-Heras, Constantin G. Daniliuc and Ryan Gilmour

ACS Catal., 2022, 12, 14507
DOI: 10.1021/acscatal.2c04511

Janus All‐Cis 2,3,4,5,6‐Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry

Joshua L. Clark, Rifahath M. Neyyappadath, Cihang Yu, Alexandra M. Z. Slawin, David B. Cordes and David O'Hagan

Chemistry A European J, 2021, 27, 16000
DOI: 10.1002/chem.202102819

Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization

You‐Jie Yu, Joel Häfliger, Zi‐Xuan Wang, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202309789

Synthetic Strategy for Unsymmetrical α-Fluoro-α′-aryl Ketones

Shubham Dutta, Avijit Maity, Shengwen Yang, Rajendra K. Mallick, Manash P. Gogoi, Vincent Gandon and Akhila K. Sahoo

Org. Lett., 2025, 27, 808
DOI: 10.1021/acs.orglett.4c04486

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

Oleksandr O. Grygorenko, Kostiantyn P. Melnykov, Serhii Holovach and Oleksandr Demchuk

ChemMedChem, 2022, 17
DOI: 10.1002/cmdc.202200365

Introducing the Cis‐2,3‐Bis(trifluoromethyl)cyclopropyl Chemotype: Late‐Stage Installation and Stereoelectronic Properties

Daniel Gaviña, Zeyu Feng, David Herrero, Martin Simon, Christopher Golz and Manuel Alcarazo

ChemistryEurope, 2026, 4
DOI: 10.1002/ceur.202500384

Catalytic Ring Expanding Difluorination: An Enantioselective Platform to Access β,β‐Difluorinated Carbocycles

Louise Ruyet, Christoph Roblick, Joel Häfliger, Zi‐Xuan Wang, Tobias Jürgen Stoffels, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2024, 63
DOI: 10.1002/anie.202403957

Acidity Controlled Formal Nucleophilic Substitution of Hydrofluoroolefin‐Based Iodonium Salt with O‐nucleophiles: Synthetic Application and Mechanistic Study

János T. Csenki, Dóra F. Englert, Dániel Steinsits, Péter P. Fehér, András Stirling and Zoltán Novák

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202502254

Catalytic Homologation‐Allylboration Sequence for Diastereo‐ and Enantioselective Synthesis of Densely Functionalized β‐Fluorohydrins with Tertiary Fluoride Stereocenters

Qiang Wang, Lars Eriksson and Kálmán J. Szabó

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202301481

Privileged Chiral Photocatalysts

Emanuel Studer, Smita Mandal, Timo Stünkel and Ryan Gilmour

Angewandte Chemie, 2025, 137
DOI: 10.1002/ange.202513320

Stereodivergent Synthesis of the Vicinal Difluorinated Tetralin of Casdatifan Enabled by Ru-Catalyzed Transfer Hydrogenation

Guillaume Mata, Artur K. Mailyan, Jeremy Fournier, Joel W. Beatty, Manmohan R. Leleti, Jay P. Powers and Kenneth V. Lawson

Org. Lett., 2025, 27, 833
DOI: 10.1021/acs.orglett.4c04501

Synthesis, Physicochemical Properties, and Computational Analysis of Tris(fluoromethyl)Alkyl Building Blocks

Denys Klyukovskyi, Oleksandr S. Liashuk, Mykhailo Redka, Alina T. Bezuhla, Oleksandr P. Blahun, Dmytro Lesyk, Petro Borysko, Anton V. Chernykh, Yurii M. Pustovit and Oleksandr O. Grygorenko

Chemistry A European J, 2026, 32
DOI: 10.1002/chem.70736

Hypervalent Iodine Mediated Ring-Opening 1,3-Difluorination of Benzylidenecyclopropanes

Long-Ling Huang, Jia-Yi Li, Qigang Sun, Gui-Yang Zhao, Honggen Wang and Qingjiang Li

Synthesis, 2025, 57, 1230
DOI: 10.1055/a-2373-0304

Regioselective fluorination of allenes enabled by I(I)/I(III) catalysis

Zi-Xuan Wang, Yameng Xu and Ryan Gilmour

Nat Commun, 2024, 15
DOI: 10.1038/s41467-024-50227-x

Catalytic Homologation‐Allylboration Sequence for Diastereo‐ and Enantioselective Synthesis of Densely Functionalized β‐Fluorohydrins with Tertiary Fluoride Stereocenters

Qiang Wang, Lars Eriksson and Kálmán J. Szabó

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202301481

Ex-situ ChloGen: A facile and straightforward entry to Aryl-IF4 compounds

Karim Ullah, Reza Kordnezhadian, Joachim Demaerel, Wim M. De Borggraeve and Ermal Ismalaj

Journal of Fluorine Chemistry, 2024, 275, 110276
DOI: 10.1016/j.jfluchem.2024.110276

Fluoro‐Fucosylation Enables the Interrogation of the Lea‐LecB Interaction by BioNMR Spectroscopy

Kathrin Siebold, Elena Chikunova, Nils Lorz, Christina Jordan, Alvar D. Gossert and Ryan Gilmour

Angew Chem Int Ed, 2025, 64
DOI: 10.1002/anie.202423782

3‐Fluoroalkyl (CF3, CHF2, CH2F) Cyclobutane‐Derived Building Blocks for Medicinal Chemistry: Synthesis and Physicochemical Properties

Oleksandr P. Demchuk, Bohdan V. Bobovskyi, Bohdan V. Vashchenko, Oleksandr V. Hryshchuk, Artem Skreminskyi, Anton V. Chernykh, Viktoriia S. Moskvina, Olga V. Hordiyenko, Dmitriy M. Volochnyuk and Oleksandr O. Grygorenko

Eur J Org Chem, 2023, 26
DOI: 10.1002/ejoc.202300292

Synthetic Strategies and Applications of Fluorine‐Containing Bridged Bicyclic Compounds

Simone Baldon, Luca Dell'Amico and Sara Cuadros

Eur J Org Chem, 2024, 27
DOI: 10.1002/ejoc.202400604

Fluoroiodomethane: A CH2F‐Moiety‐Delivering Agent Suitable for Nucleophilic‐, Electrophilic‐, and Radical‐Harnessed Operations

Raffaele Senatore, Monika Malik and Vittorio Pace

Adv Synth Catal, 2022, 364, 2890
DOI: 10.1002/adsc.202200493

Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo‐Enantiocontrolled β‐Functionalization of Enals

Ricardo I. Rodríguez, Marina Sicignano and José Alemán

Angew Chem Int Ed, 2022, 61
DOI: 10.1002/anie.202112632

Integrating I(I)/I(III) catalysis in reaction cascade design enables the synthesis of gem-difluorinated tetralins from cyclobutanols

Joel Häfliger, Louise Ruyet, Nico Stübke, Constantin G. Daniliuc and Ryan Gilmour

Nat Commun, 2023, 14
DOI: 10.1038/s41467-023-38957-w

Effect of gem‐Difluorination on the Key Physicochemical Properties Relevant to Medicinal Chemistry: The Case of Functionalized Cycloalkanes

Sergey Holovach, Kostiantyn P. Melnykov, Artem Skreminskiy, Maksym Herasymchuk, Olha Tavlui, Danylo Aloshyn, Petro Borysko, Alexander B. Rozhenko, Sergey V. Ryabukhin, Dmitriy M. Volochnyuk and Oleksandr O. Grygorenko

Chemistry A European J, 2022, 28
DOI: 10.1002/chem.202200331

A General Organophotoredox Strategy to Difluoroalkyl Bicycloalkane (CF2‐BCA) Hybrid Bioisosteres**

Sara Cuadros, Giulio Goti, Giorgia Barison, Alfredo Raulli, Tommaso Bortolato, Giorgio Pelosi, Paolo Costa and Luca Dell'Amico

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202303585

Privileged Chiral Photocatalysts

Emanuel Studer, Smita Mandal, Timo Stünkel and Ryan Gilmour

Angew Chem Int Ed, 2025, 64
DOI: 10.1002/anie.202513320

Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides

Zi‐Xuan Wang, Nele A. Heckmann, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2025, 137
DOI: 10.1002/ange.202518520

Streamlining Fluoroalkenyl Arene Synthesis Illuminated with Mechanistic Insights

Sanaz Rajabalinia, Sabrina Hoford and Travis Dudding

ACS Omega, 2024, 9, 21152
DOI: 10.1021/acsomega.4c01055

Design of robust fluorinated interpenetrating poly(thieno[3,2-b]thiophene) network for highly stable flexible electrochromic-supercapacitor devices

Chunhui Du, Hui Li, Ge Zhang, Rongtai Wan, Wanyi Zhang, Xuejiao Xu, Lu Zheng, Xukun Deng, Jingkun Xu, Baoyang Lu and Guangming Nie

Chemical Engineering Journal, 2024, 495, 153692
DOI: 10.1016/j.cej.2024.153692

Regio‐ und enantioselektive, intermolekulare Aminofluorierung von Alkenen durch Iod(I)/Iod(III)‐Katalyse**

Michael Schäfer, Timo Stünkel, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2022, 134
DOI: 10.1002/ange.202205508

Carbodefluorination of fluoroalkyl ketones via a carbene-initiated rearrangement strategy

Linxuan Li, Xinyu Zhang, Yongquan Ning, Xiaolong Zhang, Binbin Liu, Zhansong Zhang, Paramasivam Sivaguru, Giuseppe Zanoni, Shuang Li, Edward A. Anderson and Xihe Bi

Nat Commun, 2022, 13
DOI: 10.1038/s41467-022-31976-z

Forging Medium Rings via I(I)/I(III)‐Catalyzed Diene Carbofunctionalization

You‐Jie Yu, Joel Häfliger, Zi‐Xuan Wang, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202309789

Catalytic Stereoconvergent Synthesis of Homochiral β-CF3, β-SCF3, and β-OCF3 Benzylic Alcohols

Andrej Emanuel Cotman, Pavel A. Dub, Maša Sterle, Matic Lozinšek, Jaka Dernovšek, Živa Zajec, Anamarija Zega, Tihomir Tomašič and Dominique Cahard

ACS Org. Inorg. Au, 2022, 2, 396
DOI: 10.1021/acsorginorgau.2c00019

Catalytic, Regioselective 1,4‐Fluorodifunctionalization of Dienes

You‐Jie Yu, Michael Schäfer, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202214906

Enantioselective Photocatalysis Using a Privileged Al–Salen Complex

Julia Soika, Carina Onneken, Tobias Morack and Ryan Gilmour

Acc. Chem. Res., 2025, 58, 1710
DOI: 10.1021/acs.accounts.5c00194

Catalyst-Substrate Helical Character Matching Determines the Enantioselectivity in the Ishihara-Type Iodoarenes Catalyzed Asymmetric Kita-Dearomative Spirolactonization

Hanliang Zheng, Liu Cai, Ming Pan, Muhammet Uyanik, Kazuaki Ishihara and Xiao-Song Xue

J. Am. Chem. Soc., 2023, 145, 7301
DOI: 10.1021/jacs.2c13295

Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides

Zi‐Xuan Wang, Nele A. Heckmann, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2025, 64
DOI: 10.1002/anie.202518520

Iodine(III)‐Mediated Migratory gem‐Difluorinations: Synthesis of β Transformable Functionality Substituted gem‐Difluoroalkanes

Qingjiang Li, Xiao‐Bin Liu and Honggen Wang

The Chemical Record, 2023, 23
DOI: 10.1002/tcr.202300231

Fluorocyclisation of Oximes to Isoxazolines Through I(I)/I(III) Catalysis

Jessica Neufeld, Constantin G. Daniliuc and Ryan Gilmour

Helvetica Chimica Acta, 2023, 106
DOI: 10.1002/hlca.202200183

Asymmetric Synthesis of Monofluorinated Carbocyclic Alcohols and Vicinal Difluorinated Heterocycles and Carbocycles

Lucas Bacheley, Ricardo Molina Betancourt, Rathies Ravindra, Gérard Guillamot, Phannarath Phansavath and Virginie Ratovelomanana‐Vidal

Eur J Org Chem, 2023, 26
DOI: 10.1002/ejoc.202300383

Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo‐Enantiocontrolled β‐Functionalization of Enals

Ricardo I. Rodríguez, Marina Sicignano and José Alemán

Angewandte Chemie, 2022, 134
DOI: 10.1002/ange.202112632

Trifluorination of 1,1-Diarylethenes Using Selectfluor/HF Reagent and Experimental Evidence for a Single Electron Transfer Mechanism

Tsugio Kitamura, Juzo Oyamada, Masahiro Higashi and Yosuke Kishikawa

J. Org. Chem., 2026
DOI: 10.1021/acs.joc.6c00562

Catalytic, Regioselective 1,4‐Fluorodifunctionalization of Dienes

You‐Jie Yu, Michael Schäfer, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202214906

F-CPI: A Multimodal Deep Learning Approach for Predicting Compound Bioactivity Changes Induced by Fluorine Substitution

Qian Zhang, Wenhai Yin, Xinyao Chen, Aimin Zhou, Guixu Zhang, Zhi Zhao, Zhiqiang Li, Yan Zhang, Samuel Jacob Bunu, Jingshan Shen, Weiliang Zhu, Xiangrui Jiang and Zhijian Xu

J. Med. Chem., 2025, 68, 706
DOI: 10.1021/acs.jmedchem.4c02668

Metal-Free C–H Difluoromethylation of Imidazoles with the Ruppert–Prakash Reagent

Denys A. Kvasha, Andrii Deviatkin, Andrii S. Poturai, Pavel S. Nosik, Andrii A. Kyrylchuk, Sergiy Suikov, Alexander B. Rozhenko, Dmitriy M. Volochnyuk and Oleksandr O. Grygorenko

J. Org. Chem., 2023, 88, 163
DOI: 10.1021/acs.joc.2c02041

Enyne difluorination

Rachel C. Epplin and Tanja Gulder

Nat. Chem., 2023, 15, 1484
DOI: 10.1038/s41557-023-01352-5

Stereocontrolled Synthesis of Fluorinated Isochromans via Iodine(I)/Iodine(III) Catalysis

Joel Häfliger, Olga O. Sokolova, Madina Lenz, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2022, 61
DOI: 10.1002/anie.202205277

In Situ Generated DBU⋅HF Acts as a Fluorinating Agent in a Hexafluoroisobutylation Tandem Reaction: An Effective Route to 5,5,5,5’,5’,5’‐Hexafluoroleucine

Guillaume Naulet, Aline Delamare, Gilles Guichard and Guillaume Compain

Eur J Org Chem, 2023, 26
DOI: 10.1002/ejoc.202201148

Fluor‐Fucosylierung ermöglicht die Untersuchung der Lea‐LecB‐Wechselwirkung durch BioNMR‐Spektroskopie

Kathrin Siebold, Elena Chikunova, Nils Lorz, Christina Jordan, Alvar D. Gossert and Ryan Gilmour

Angewandte Chemie, 2025, 137
DOI: 10.1002/ange.202423782

Conformational Analysis of 1,3-Difluorinated Alkanes

William G. Poole, Florent Peron, Stephen J. Fox, Neil Wells, Chris-Kriton Skylaris, Jonathan W. Essex, Ilya Kuprov and Bruno Linclau

J. Org. Chem., 2024, 89, 8789
DOI: 10.1021/acs.joc.4c00670

A General Organophotoredox Strategy to Difluoroalkyl Bicycloalkane (CF2‐BCA) Hybrid Bioisosteres**

Sara Cuadros, Giulio Goti, Giorgia Barison, Alfredo Raulli, Tommaso Bortolato, Giorgio Pelosi, Paolo Costa and Luca Dell'Amico

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202303585

Regioselective, catalytic 1,1-difluorination of enynes

Zi-Xuan Wang, Keith Livingstone, Carla Hümpel, Constantin G. Daniliuc, Christian Mück-Lichtenfeld and Ryan Gilmour

Nat. Chem., 2023, 15, 1515
DOI: 10.1038/s41557-023-01344-5

Stereokontrollierte Synthese von fluorierten Isochromanen durch Iod(I)/Iod(III)‐Katalyse

Joel Häfliger, Olga O. Sokolova, Madina Lenz, Constantin G. Daniliuc and Ryan Gilmour

Angewandte Chemie, 2022, 134
DOI: 10.1002/ange.202205277

Regio‐ and Enantioselective Intermolecular Aminofluorination of Alkenes via Iodine(I)/Iodine(III) Catalysis**

Michael Schäfer, Timo Stünkel, Constantin G. Daniliuc and Ryan Gilmour

Angew Chem Int Ed, 2022, 61
DOI: 10.1002/anie.202205508