Organo-fluorine chemistry V

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Editor: Prof. David O'Hagan
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.

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Organo-fluorine chemistry V

  • David O’Hagan

Beilstein J. Org. Chem. 2021, 17, 737–738, doi:10.3762/bjoc.17.63

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Published 17 Mar 2021

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

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Published 07 Apr 2020

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

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Published 08 Apr 2020

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

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Published 14 Apr 2020

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

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Published 16 Apr 2020

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

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Published 20 Apr 2020

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

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Published 15 May 2020

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

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Published 29 May 2020

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

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Published 29 Jun 2020

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

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Published 30 Jun 2020

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

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Published 10 Jul 2020

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

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Published 14 Jul 2020

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

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Published 23 Jul 2020

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

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Published 07 Aug 2020

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

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Published 11 Aug 2020

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

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Published 02 Sep 2020

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

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Published 02 Sep 2020

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

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Published 03 Sep 2020

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

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Published 04 Sep 2020

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

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Published 17 Sep 2020

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

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Published 30 Sep 2020

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

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Published 05 Oct 2020

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

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Published 16 Oct 2020

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

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Published 23 Oct 2020

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

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Published 28 Oct 2020

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

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Published 29 Oct 2020

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

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Published 11 Nov 2020

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

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Published 25 Nov 2020

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

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Published 01 Dec 2020

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

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Published 10 Dec 2020

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

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Published 14 Dec 2020

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

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Published 16 Dec 2020

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

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Published 29 Dec 2020

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

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Published 08 Jan 2021

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

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Published 11 Jan 2021

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

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Published 15 Jan 2021
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Published 21 Jan 2021

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

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Published 25 Jan 2021

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

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Published 27 Jan 2021

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

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Published 28 Jan 2021

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

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Published 03 Feb 2021

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

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Published 09 Feb 2021

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

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Published 12 Feb 2021

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

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Published 15 Feb 2021

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

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Published 19 Feb 2021

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

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Published 24 Feb 2021

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

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