TY - JOUR
T1 - Organofluorine chemistry
T2 - Promising growth areas and challenges
AU - Politanskaya, Larisa V.
AU - Selivanova, Galina A.
AU - Panteleeva, Elena V.
AU - Tretyakov, Evgeny V.
AU - Platonov, Vyacheslav E.
AU - Nikul'Shin, Pavel V.
AU - Vinogradov, Andrey S.
AU - Zonov, Yaroslav V.
AU - Karpov, Victor M.
AU - Mezhenkova, Tatyana V.
AU - Vasilyev, Aleksander V.
AU - Koldobskii, Andrei B.
AU - Shilova, Olga S.
AU - Morozova, Sofia M.
AU - Burgart, Yanina V.
AU - Shchegolkov, Evgeny V.
AU - Saloutin, Victor I.
AU - Sokolov, Vladimir B.
AU - Aksinenko, Aleksey Yu
AU - Nenajdenko, Valentine G.
AU - Moskalik, Mikhail Yu
AU - Astakhova, Vera V.
AU - Shainyan, Bagrat A.
AU - Tabolin, Andrey A.
AU - Ioffe, Sema L.
AU - Muzalevskiy, Vasiliy M.
AU - Balenkova, Elizaveta S.
AU - Shastin, Alexey V.
AU - Tyutyunov, Andrey A.
AU - Boiko, Vladimir E.
AU - Igumnov, Sergei M.
AU - Dilman, Alexander D.
AU - Adonin, Nicolay Yu
AU - Bardin, Vadim V.
AU - Masoud, Salekh M.
AU - Vorobyeva, Daria V.
AU - Osipov, Sergey N.
AU - Nosova, Emiliya V.
AU - Lipunova, Galina N.
AU - Charushin, Valery N.
AU - Prima, Darya O.
AU - Makarov, Arkady G.
AU - Zibarev, Andrey V.
AU - Trofimov, Boris A.
AU - Sobenina, Lyubov N.
AU - Belyaeva, Kseniya V.
AU - Sosnovskikh, Vyacheslav Ya
AU - Obydennov, Dmitrii L.
AU - Usachev, Sergey A.
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Currently, the chemistry of organofluorine compounds is a leading and rapidly developing area of organic chemistry. Fluorine present in a molecule largely determines its specific chemical and biological properties. This thematic issue covers the trends of organofluorine chemistry that have been actively developed in Russia the last 15 ± 20 years. The review describes nucleophilic substitution and heterocyclization reactions involving fluorinated arenes and quinones and skeletal cationoid rearrangements in the polyfluoroarene series. The transformations involving CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and trans- formations of the organic moiety in polyfluorinated organoboranes and borates with retention of the carbon - boron bond are discussed. Particular attention is devoted to catalytic olefination using freons as an efficient synthetic route to fluorinated compounds. The application of unsymmetrical fluorine-containing N-heterocyclic carbene ligands as catalysts for olefin metathesis is demonstrated. A variety of classes of organofluorine compounds are considered, in particular, polyfluorinated arenes and 1,2-diaminobenzenes, 1-halo-2-trifluoroacetylacetylenes, α-fluoronitro compounds, fluorinated heterocycles, 2-hydrazinylidene-1,3-dicarbonyl derivatives, imines and silanes. The potential practical applications of organofluorine compounds in fundamental organic chemistry, materials science and biomedicine are outlined.
AB - Currently, the chemistry of organofluorine compounds is a leading and rapidly developing area of organic chemistry. Fluorine present in a molecule largely determines its specific chemical and biological properties. This thematic issue covers the trends of organofluorine chemistry that have been actively developed in Russia the last 15 ± 20 years. The review describes nucleophilic substitution and heterocyclization reactions involving fluorinated arenes and quinones and skeletal cationoid rearrangements in the polyfluoroarene series. The transformations involving CF3-substituted carbocations and radical cations are considered. Heterocyclization and oxidative addition reactions of trifluoroacetamide derivatives and trans- formations of the organic moiety in polyfluorinated organoboranes and borates with retention of the carbon - boron bond are discussed. Particular attention is devoted to catalytic olefination using freons as an efficient synthetic route to fluorinated compounds. The application of unsymmetrical fluorine-containing N-heterocyclic carbene ligands as catalysts for olefin metathesis is demonstrated. A variety of classes of organofluorine compounds are considered, in particular, polyfluorinated arenes and 1,2-diaminobenzenes, 1-halo-2-trifluoroacetylacetylenes, α-fluoronitro compounds, fluorinated heterocycles, 2-hydrazinylidene-1,3-dicarbonyl derivatives, imines and silanes. The potential practical applications of organofluorine compounds in fundamental organic chemistry, materials science and biomedicine are outlined.
KW - FLUORINE-CONTAINING HETEROCYCLES
KW - BIOLOGICALLY-ACTIVE AMIDES
KW - ONE-POT SYNTHESIS
KW - BETA-ARYL ENAMINES
KW - CONTAINING 2-ARYLHYDRAZONO-1,3-DICARBONYL COMPOUNDS
KW - PALLADIUM-CATALYZED DIFLUOROMETHYLATION
KW - DIRECT NUCLEOPHILIC DIFLUOROMETHYLATION
KW - COPPER-MEDIATED DIFLUOROMETHYLATION
KW - GRUBBS 2ND-GENERATION CATALYST
KW - ASYMMETRIC MICHAEL ADDITION
UR - http://www.scopus.com/inward/record.url?scp=85066251313&partnerID=8YFLogxK
U2 - 10.1070/RCR4871
DO - 10.1070/RCR4871
M3 - Review article
AN - SCOPUS:85066251313
VL - 88
SP - 425
EP - 569
JO - Russian Chemical Reviews
JF - Russian Chemical Reviews
SN - 0036-021X
IS - 5
ER -