Organo-fluorine chemistry III

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Editor: Prof. David O'Hagan
University of St Andrews
 
This is the third in the series of Thematic Issues on organo-fluorine chemistry for this journal. Fluorine touches all categories of performance compounds extending from bioactives to organic materials, and society demands continual improvements in the quality and performance of products and devices. This requires innovation in molecular design, and because of its particular ability to tune properties, fluorine chemistry may provide the means. To meet these demands we continually need new methods and new building blocks to prepare new classes of compounds. As our ability to prepare and apply organo-fluorine molecules improves, it demands a deeper understanding of their properties and behaviour. The papers of the Thematic Series touch on all of these aspects and the area remains as innovative and relevant as ever.

See also the Thematic Series:
Organo-fluorine chemistry II
Organo-fluorine chemistry

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Organo-fluorine chemistry III

  • David O'Hagan

Beilstein J. Org. Chem. 2013, 9, 2180–2181, doi:10.3762/bjoc.9.255

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Published 23 Oct 2013

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

  • Assaad Nasr El Dine,
  • Ali Khalaf,
  • Danielle Grée,
  • Olivier Tasseau,
  • Fares Fares,
  • Nada Jaber,
  • Philippe Lesot,
  • Ali Hachem and
  • René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

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Published 26 Sep 2013

Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

  • Holger Erdbrink,
  • Elisabeth K. Nyakatura,
  • Susanne Huhmann,
  • Ulla I. M. Gerling,
  • Dieter Lentz,
  • Beate Koksch and
  • Constantin Czekelius

Beilstein J. Org. Chem. 2013, 9, 2009–2014, doi:10.3762/bjoc.9.236

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Published 02 Oct 2013

Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne

  • Motoki Naka,
  • Tomoko Kawasaki-Takasuka and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2013, 9, 2182–2188, doi:10.3762/bjoc.9.256

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Published 23 Oct 2013

Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system

  • Satoshi Okusu,
  • Yutaka Sugita,
  • Etsuko Tokunaga and
  • Norio Shibata

Beilstein J. Org. Chem. 2013, 9, 2189–2193, doi:10.3762/bjoc.9.257

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Published 23 Oct 2013

Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide

  • Sébastien Alazet,
  • Kevin Ollivier and
  • Thierry Billard

Beilstein J. Org. Chem. 2013, 9, 2354–2357, doi:10.3762/bjoc.9.270

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Published 04 Nov 2013

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

  • Peer Kirsch,
  • Qiong Tong and
  • Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

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Published 05 Nov 2013

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

  • Raoni S. B. Gonçalves,
  • Michael Dos Santos,
  • Guillaume Bernadat,
  • Danièle Bonnet-Delpon and
  • Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

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Published 07 Nov 2013

Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

  • Yuzo Nakamura,
  • Motohiro Fujiu,
  • Tatsuya Murase,
  • Yoshimitsu Itoh,
  • Hiroki Serizawa,
  • Kohsuke Aikawa and
  • Koichi Mikami

Beilstein J. Org. Chem. 2013, 9, 2404–2409, doi:10.3762/bjoc.9.277

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Published 08 Nov 2013

Oxidative 3,3,3-trifluoropropylation of arylaldehydes

  • Akari Ikeda,
  • Masaaki Omote,
  • Shiho Nomura,
  • Miyuu Tanaka,
  • Atsushi Tarui,
  • Kazuyuki Sato and
  • Akira Ando

Beilstein J. Org. Chem. 2013, 9, 2417–2421, doi:10.3762/bjoc.9.279

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Published 11 Nov 2013

Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

  • Pier Alexandre Champagne,
  • Alexandre Saint-Martin,
  • Mélina Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2013, 9, 2451–2456, doi:10.3762/bjoc.9.283

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Published 13 Nov 2013

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

  • Ju Hee Kim,
  • Su Jeong Choi and
  • In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

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Published 14 Nov 2013

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

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Published 15 Nov 2013

Reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiethane with N-vinyl compounds

  • Viacheslav A. Petrov and
  • Will Marshall

Beilstein J. Org. Chem. 2013, 9, 2615–2619, doi:10.3762/bjoc.9.295

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Published 21 Nov 2013

Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent

  • Xiao-Ping Wang,
  • Jin-Hong Lin,
  • Cheng-Pan Zhang,
  • Ji-Chang Xiao and
  • Xing Zheng

Beilstein J. Org. Chem. 2013, 9, 2635–2640, doi:10.3762/bjoc.9.299

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Published 25 Nov 2013

Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate

  • James A. B. Laurenson,
  • John A. Parkinson,
  • Jonathan M. Percy,
  • Giuseppe Rinaudo and
  • Ricard Roig

Beilstein J. Org. Chem. 2013, 9, 2660–2668, doi:10.3762/bjoc.9.301

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Published 26 Nov 2013

Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines

  • Alexander Penger,
  • Cortney N. von Hahmann,
  • Alexander S. Filatov and
  • John T. Welch

Beilstein J. Org. Chem. 2013, 9, 2675–2680, doi:10.3762/bjoc.9.303

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Published 27 Nov 2013

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

  • Santos Fustero,
  • Paula Bello,
  • Javier Miró,
  • María Sánchez-Roselló,
  • Günter Haufe and
  • Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

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Published 28 Nov 2013

Stereoselectively fluorinated N-heterocycles: a brief survey

  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

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Published 29 Nov 2013

Flow microreactor synthesis in organo-fluorine chemistry

  • Hideki Amii,
  • Aiichiro Nagaki and
  • Jun-ichi Yoshida

Beilstein J. Org. Chem. 2013, 9, 2793–2802, doi:10.3762/bjoc.9.314

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Published 05 Dec 2013

Modulating NHC catalysis with fluorine

  • Yannick P. Rey and
  • Ryan Gilmour

Beilstein J. Org. Chem. 2013, 9, 2812–2820, doi:10.3762/bjoc.9.316

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Published 06 Dec 2013

Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF3

  • Xueliang Jiang and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2013, 9, 2862–2865, doi:10.3762/bjoc.9.322

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Published 12 Dec 2013

Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxol-3-one

  • Nico Santschi,
  • Roman C. Sarott,
  • Elisabeth Otth,
  • Reinhard Kissner and
  • Antonio Togni

Beilstein J. Org. Chem. 2014, 10, 1–6, doi:10.3762/bjoc.10.1

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Published 02 Jan 2014

The difluoromethylene (CF2) group in aliphatic chains: Synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groups

  • Yi Wang,
  • Ricardo Callejo,
  • Alexandra M. Z. Slawin and
  • David O’Hagan

Beilstein J. Org. Chem. 2014, 10, 18–25, doi:10.3762/bjoc.10.4

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Published 06 Jan 2014

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

  • Kazutaka Shibatomi,
  • Takuya Okimi,
  • Yoshiyuki Abe,
  • Akira Narayama,
  • Nami Nakamura and
  • Seiji Iwasa

Beilstein J. Org. Chem. 2014, 10, 323–331, doi:10.3762/bjoc.10.30

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Published 04 Feb 2014

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

  • Fei Wang,
  • Lingchun Li,
  • Chuanfa Ni and
  • Jinbo Hu

Beilstein J. Org. Chem. 2014, 10, 344–351, doi:10.3762/bjoc.10.32

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Published 06 Feb 2014

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

  • Natalia V. Pavlenko,
  • Tatiana I. Oos,
  • Yurii L. Yagupolskii,
  • Igor I. Gerus,
  • Uwe Doeller and
  • Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

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Published 26 Mar 2014

Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester

  • Antal Harsanyi,
  • Graham Sandford,
  • Dmitri S. Yufit and
  • Judith A.K. Howard

Beilstein J. Org. Chem. 2014, 10, 1213–1219, doi:10.3762/bjoc.10.119

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Published 22 May 2014
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