Organo-fluorine chemistry V
University of St Andrews
This is the fifth thematic issue on organo-fluorine chemistry in the Beilstein Journal of Organic Chemistry that I have had the pleasure to edit, and these themed issues have gone progressively from strength to strength ever since the first was assembled in 2008. In this issue 46 papers are collected, a record for a thematic issue in the Journal, and there is no doubt that the Beilstein Journal of Organic Chemistry has become a settled home for papers in contemporary organo-fluorine chemistry. Authors have presented their recent findings or, in some cases, reviewed important areas, from bioactives to materials, and collectively the papers highlight the vibrancy and range of activity associated with this theme. Organo-fluorine chemistry merits our attention as an important discipline within contemporary organic chemistry contributing in a unique way to innovation and performance in the development of functional molecules.
This issue will be historically memorable as all of the manuscripts were submitted through the covid-19 virus lockdown period which impacted universities and research laboratories across the world. As Guest Editor I am indebted to all of the authors for maintaining their commitment to contribute through what was a particularly difficult and unusual period of professional life.
Organo-fluorine chemistry V
- David O’Hagan
Beilstein J. Org. Chem. 2021, 17, 737–738, doi:10.3762/bjoc.17.63
Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis
- Xing-Fa Tan,
- Fa-Guang Zhang and
- Jun-An Ma
Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60
Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles
- Ming-Xi Bi,
- Shuai Liu,
- Yangen Huang,
- Xiu-Hua Xu and
- Feng-Ling Qing
Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62
Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes
- Zeguo Fang,
- Nawaf Al-Maharik,
- Peer Kirsch,
- Matthias Bremer,
- Alexandra M. Z. Slawin and
- David O’Hagan
Beilstein J. Org. Chem. 2020, 16, 674–680, doi:10.3762/bjoc.16.65
Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
- Marcin Kaźmierczak and
- Henryk Koroniak
Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69
Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K2CO3/n-Bu4PBr in water
- Thanigaimalai Pillaiyar,
- Masoud Sedaghati and
- Gregor Schnakenburg
Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71
Fluorinated phenylalanines: synthesis and pharmaceutical applications
- Laila F. Awad and
- Mohammed Salah Ayoup
Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91
Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
- Shigeyuki Yamada,
- Takuya Higashida,
- Yizhou Wang,
- Masato Morita,
- Takuya Hosokai,
- Kaveendra Maduwantha,
- Kaveenga Rasika Koswattage and
- Tsutomu Konno
Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102
Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers
- Vyacheslav I. Supranovich,
- Vitalij V. Levin and
- Alexander D. Dilman
Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126
NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
- Alyn T. Davies,
- Mark D. Greenhalgh,
- Alexandra M. Z. Slawin and
- Andrew D. Smith
Beilstein J. Org. Chem. 2020, 16, 1572–1578, doi:10.3762/bjoc.16.129
Fluorohydration of alkynes via I(I)/I(III) catalysis
- Jessica Neufeld,
- Constantin G. Daniliuc and
- Ryan Gilmour
Beilstein J. Org. Chem. 2020, 16, 1627–1635, doi:10.3762/bjoc.16.135
Pauson–Khand reaction of fluorinated compounds
- Jorge Escorihuela,
- Daniel M. Sedgwick,
- Alberto Llobat,
- Mercedes Medio-Simón,
- Pablo Barrio and
- Santos Fustero
Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138
Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines
- Vladimir Kubyshkin
Beilstein J. Org. Chem. 2020, 16, 1837–1852, doi:10.3762/bjoc.16.151
Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions
- Clément Q. Fontenelle,
- Thibault Thierry,
- Romain Laporte,
- Emmanuel Pfund and
- Thierry Lequeux
Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160
Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination
- Yuqing Wang,
- Gaigai Wang,
- Anatoly A. Peshkov,
- Ruwei Yao,
- Muhammad Hasan,
- Manzoor Zaman,
- Chao Liu,
- Stepan Kashtanov,
- Olga P. Pereshivko and
- Vsevolod A. Peshkov
Beilstein J. Org. Chem. 2020, 16, 1963–1973, doi:10.3762/bjoc.16.163
Synthesis of 6,13-difluoropentacene
- Matthias W. Tripp and
- Ulrich Koert
Beilstein J. Org. Chem. 2020, 16, 2136–2140, doi:10.3762/bjoc.16.181
Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups
- Benjamin Jeffries,
- Zhong Wang,
- Robert I. Troup,
- Anaïs Goupille,
- Jean-Yves Le Questel,
- Charlene Fallan,
- James S. Scott,
- Elisabetta Chiarparin,
- Jérôme Graton and
- Bruno Linclau
Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182
Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis
- Shahboz Yakubov and
- Joshua P. Barham
Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183
Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols
- Tatsuya Kumon,
- Miroku Shimada,
- Jianyan Wu,
- Shigeyuki Yamada and
- Tsutomu Konno
Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184
Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
- Viktor M. Tkachuk,
- Oleh O. Lukianov,
- Mykhailo V. Vovk,
- Isabelle Gillaizeau and
- Volodymyr A. Sukach
Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191
Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent
- Tatsuhiro Uchikura,
- Nanami Kamiyama,
- Taisuke Ishikawa and
- Takahiko Akiyama
Beilstein J. Org. Chem. 2020, 16, 2442–2447, doi:10.3762/bjoc.16.198
Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction
- Daniela Rodrigues Silva,
- Joyce K. Daré and
- Matheus P. Freitas
Beilstein J. Org. Chem. 2020, 16, 2469–2476, doi:10.3762/bjoc.16.200
Synthesis of novel fluorinated building blocks via halofluorination and related reactions
- Attila Márió Remete,
- Tamás T. Novák,
- Melinda Nonn,
- Matti Haukka,
- Ferenc Fülöp and
- Loránd Kiss
Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208
Activation of pentafluoropropane isomers at a nanoscopic aluminum chlorofluoride: hydrodefluorination versus dehydrofluorination
- Maëva-Charlotte Kervarec,
- Thomas Braun,
- Mike Ahrens and
- Erhard Kemnitz
Beilstein J. Org. Chem. 2020, 16, 2623–2635, doi:10.3762/bjoc.16.213
Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity
- Yuvixza Lizarme-Salas,
- Alexandra Daryl Ariawan,
- Ranjala Ratnayake,
- Hendrik Luesch,
- Angela Finch and
- Luke Hunter
Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216
Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles
- Ziyi Li,
- Li Wang,
- Yunqi Huang,
- Haibo Mei,
- Hiroyuki Konno,
- Hiroki Moriwaki,
- Vadim A. Soloshonok and
- Jianlin Han
Beilstein J. Org. Chem. 2020, 16, 2671–2678, doi:10.3762/bjoc.16.217
Synthesis of purines and adenines containing the hexafluoroisopropyl group
- Viacheslav Petrov,
- Rebecca J. Dooley,
- Alexander A. Marchione,
- Elizabeth L. Diaz,
- Brittany S. Clem and
- William Marshall
Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose
- Danny Lainé,
- Vincent Denavit,
- Olivier Lessard,
- Laurie Carrier,
- Charles-Émile Fecteau,
- Paul A. Johnson and
- Denis Giguère
Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237
Controlled decomposition of SF6 by electrochemical reduction
- Sébastien Bouvet,
- Bruce Pégot,
- Stéphane Sengmany,
- Erwan Le Gall,
- Eric Léonel,
- Anne-Marie Goncalves and
- Emmanuel Magnier
Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244
Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate
- Kevin Grollier,
- Alexis Taponard,
- Arnaud De Zordo-Banliat,
- Emmanuel Magnier and
- Thierry Billard
Beilstein J. Org. Chem. 2020, 16, 3032–3037, doi:10.3762/bjoc.16.252
Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions
- Yumeng Liang,
- Akihito Taya,
- Zhengyu Zhao,
- Norimichi Saito and
- Norio Shibata
Beilstein J. Org. Chem. 2020, 16, 3052–3058, doi:10.3762/bjoc.16.254
Amine–borane complex-initiated SF5Cl radical addition on alkenes and alkynes
- Audrey Gilbert,
- Pauline Langowski,
- Marine Delgado,
- Laurent Chabaud,
- Mathieu Pucheault and
- Jean-François Paquin
Beilstein J. Org. Chem. 2020, 16, 3069–3077, doi:10.3762/bjoc.16.256
Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
- Vyacheslav I. Supranovich,
- Igor A. Dmitriev and
- Alexander D. Dilman
Beilstein J. Org. Chem. 2020, 16, 3104–3108, doi:10.3762/bjoc.16.260
Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
- Armin Ariamajd,
- Nils J. Gerwien,
- Benjamin Schwabe,
- Stefan Dix and
- Matthew N. Hopkinson
Beilstein J. Org. Chem. 2021, 17, 83–88, doi:10.3762/bjoc.17.8
Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane
- Yukiko Karuo,
- Ayaka Kametani,
- Atsushi Tarui,
- Kazuyuki Sato,
- Kentaro Kawai and
- Masaaki Omote
Beilstein J. Org. Chem. 2021, 17, 89–96, doi:10.3762/bjoc.17.9
Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds
- Takashi Yamazaki,
- Yoh Nakajima,
- Minato Iida and
- Tomoko Kawasaki-Takasuka
Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14
Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation
- Dongyang Chen and
- Eli Zysman-Colman
Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21
Decarboxylative trifluoromethylthiolation of pyridylacetates
- Ryouta Kawanishi,
- Kosuke Nakada and
- Kazutaka Shibatomi
Beilstein J. Org. Chem. 2021, 17, 229–233, doi:10.3762/bjoc.17.23
Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
- Savva A. Ponomarev,
- Roman V. Larkovich,
- Alexander S. Aldoshin,
- Andrey A. Tabolin,
- Sema L. Ioffe,
- Jonathan Groß,
- Till Opatz and
- Valentine G. Nenajdenko
Beilstein J. Org. Chem. 2021, 17, 283–292, doi:10.3762/bjoc.17.27
19F NMR as a tool in chemical biology
- Diana Gimenez,
- Aoife Phelan,
- Cormac D. Murphy and
- Steven L. Cobb
Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28
CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry
- Anthony J. Fernandes,
- Armen Panossian,
- Bastien Michelet,
- Agnès Martin-Mingot,
- Frédéric R. Leroux and
- Sébastien Thibaudeau
Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32
Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]
- Takeshi Fujita,
- Noriaki Shoji,
- Nao Yoshikawa and
- Junji Ichikawa
Beilstein J. Org. Chem. 2021, 17, 396–403, doi:10.3762/bjoc.17.35
Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system
- Yamato Fujihira,
- Yumeng Liang,
- Makoto Ono,
- Kazuki Hirano,
- Takumi Kagawa and
- Norio Shibata
Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39
Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement
- Vladimir Kubyshkin,
- Rebecca Davis and
- Nediljko Budisa
Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40
Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting
- Masayori Hagimori,
- Estefanía E. Mendoza-Ortega and
- Marie Pierre Krafft
Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45
Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes
- Xiaojuan Li,
- Qiang Zhang,
- Weigang Zhang,
- Jinzhu Ma,
- Yi Wang and
- Yi Pan
Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49
Development of N-F fluorinating agents and their fluorinations: Historical perspective
- Teruo Umemoto,
- Yuhao Yang and
- Gerald B. Hammond
Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123
