Organo-fluorine chemistry IV
University of St Andrews
The introduction of fluorine into organic molecules is widely practised particularly when tuning the properties of molecules for specialist functions. Fluorine substitution finds a prominent role in pharmaceutical development, in governing bioactivity in a wide range of agrochemical products, in soft materials chemistry such as liquid crystals, in photoresist polymers, self-assembling monolayers and in positron emission tomography. Allied to this breadth of activity is a steady development in the number and range of fluorination reagents and methods. This Thematic Series aims to provide an insight into these developments.
Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains
- Layal Hariss,
- Kamal Bou Hadir,
- Mirvat El-Masri,
- Thierry Roisnel,
- René Grée and
- Ali Hachem
Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208
Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines
- Satoru Mori and
- Norio Shibata
Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224
Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides
- Peter T. Kaplan,
- Jessica A. Lloyd,
- Mason T. Chin and
- David A. Vicic
Beilstein J. Org. Chem. 2017, 13, 2297–2303, doi:10.3762/bjoc.13.225
Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis
- Raju Cheerlavancha,
- Ahmed Ahmed,
- Yun Cheuk Leung,
- Aggie Lawer,
- Qing-Quan Liu,
- Marina Cagnes,
- Hee-Chan Jang,
- Xiang-Guo Hu and
- Luke Hunter
Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228
Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence
- Attila Márió Remete,
- Melinda Nonn,
- Santos Fustero,
- Matti Haukka,
- Ferenc Fülöp and
- Loránd Kiss
Beilstein J. Org. Chem. 2017, 13, 2364–2371, doi:10.3762/bjoc.13.233
Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models
- Vladimir Kubyshkin and
- Nediljko Budisa
Beilstein J. Org. Chem. 2017, 13, 2442–2457, doi:10.3762/bjoc.13.241
Diastereoselective Mannich reactions of pseudo-C2-symmetric glutarimide with activated imines
- Tatsuya Ishikawa,
- Tomoko Kawasaki-Takasuka,
- Toshio Kubota and
- Takashi Yamazaki
Beilstein J. Org. Chem. 2017, 13, 2473–2477, doi:10.3762/bjoc.13.244
Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity
- Tathagata Mukherjee,
- Soumik Biswas,
- Andreas Ehnbom,
- Subrata K. Ghosh,
- Ibrahim El-Zoghbi,
- Nattamai Bhuvanesh,
- Hassan S. Bazzi and
- John A. Gladysz
Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246
One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent
- Azim Ziyaei Halimehjani,
- Martin Dračínský and
- Petr Beier
Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247
Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides
- Tao Fan,
- Wei-Dong Meng and
- Xingang Zhang
Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258
Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones
- Sergii V. Melnykov,
- Andrii S. Pataman,
- Yurii V. Dmytriv,
- Svitlana V. Shishkina,
- Mykhailo V. Vovk and
- Volodymyr A. Sukach
Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259
Electrophilic trifluoromethylselenolation of terminal alkynes with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
- Clément Ghiazza,
- Anis Tlili and
- Thierry Billard
Beilstein J. Org. Chem. 2017, 13, 2626–2630, doi:10.3762/bjoc.13.260
Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres
- Myriam Drouin and
- Jean-François Paquin
Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262
Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes
- Takeshi Fujita,
- Ryo Kinoshita,
- Tsuyoshi Takanohashi,
- Naoto Suzuki and
- Junji Ichikawa
Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266
Development of a fluorogenic small substrate for dipeptidyl peptidase-4
- Futa Ogawa,
- Masanori Takeda,
- Kanae Miyanaga,
- Keita Tani,
- Ryuji Yamazawa,
- Kiyoshi Ito,
- Atsushi Tarui,
- Kazuyuki Sato and
- Masaaki Omote
Beilstein J. Org. Chem. 2017, 13, 2690–2697, doi:10.3762/bjoc.13.267
CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na
- Hélène Guyon,
- Hélène Chachignon and
- Dominique Cahard
Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272
CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl
- Hélène Chachignon,
- Hélène Guyon and
- Dominique Cahard
Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273
The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands
- Yaochun Xu,
- Isabelle Correia,
- Tap Ha-Duong,
- Nadjib Kihal,
- Jean-Louis Soulier,
- Julia Kaffy,
- Benoît Crousse,
- Olivier Lequin and
- Sandrine Ongeri
Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276
Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion
- Susanne Huhmann,
- Anne-Katrin Stegemann,
- Kristin Folmert,
- Damian Klemczak,
- Johann Moschner,
- Michelle Kube and
- Beate Koksch
Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279
The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers
- Robert Szpera,
- Nadia Kovalenko,
- Kalaiselvi Natarajan,
- Nina Paillard and
- Bruno Linclau
Beilstein J. Org. Chem. 2017, 13, 2883–2887, doi:10.3762/bjoc.13.280
Conformational preferences of α-fluoroketones may influence their reactivity
- Graham Pattison
Beilstein J. Org. Chem. 2017, 13, 2915–2921, doi:10.3762/bjoc.13.284
Microfluidic radiosynthesis of [18F]FEMPT, a high affinity PET radiotracer for imaging serotonin receptors
- Thomas Lee Collier,
- Steven H. Liang,
- J. John Mann,
- Neil Vasdev and
- J. S. Dileep Kumar
Beilstein J. Org. Chem. 2017, 13, 2922–2927, doi:10.3762/bjoc.13.285
Stereochemical outcomes of C–F activation reactions of benzyl fluoride
- Neil S. Keddie,
- Pier Alexandre Champagne,
- Justine Desroches,
- Jean-François Paquin and
- David O'Hagan
Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6
Gram-scale preparation of negative-type liquid crystals with a CF2CF2-carbocycle unit via an improved short-step synthetic protocol
- Tatsuya Kumon,
- Shohei Hashishita,
- Takumi Kida,
- Shigeyuki Yamada,
- Takashi Ishihara and
- Tsutomu Konno
Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10
Progress in copper-catalyzed trifluoromethylation
- Guan-bao Li,
- Chao Zhang,
- Chun Song and
- Yu-dao Ma
Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11
Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides
- Masanori Inaba,
- Tatsuya Sakai,
- Shun Shinada,
- Tsuyuka Sugiishi,
- Yuta Nishina,
- Norio Shibata and
- Hideki Amii
Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12
Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes
- Anna-Lena Dreier,
- Andrej V. Matsnev,
- Joseph S. Thrasher and
- Günter Haufe
Beilstein J. Org. Chem. 2018, 14, 373–380, doi:10.3762/bjoc.14.25
Synthesis and stability of strongly acidic benzamide derivatives
- Frederik Diness,
- Niels J. Bjerrum and
- Mikael Begtrup
Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38
Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc
- Kohsuke Aikawa,
- Kohei Yabuuchi,
- Kota Torii and
- Koichi Mikami
Beilstein J. Org. Chem. 2018, 14, 576–582, doi:10.3762/bjoc.14.44
