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Modular Construction of Fluoroarenes from a New Difluorinated Building Block by Cross‐Coupling/Electrocyclisation/Dehydrofluorination Reactions
Author(s) -
Percy Jonathan M.,
Emerson Helena,
Fyfe James W. B.,
Kennedy Alan R.,
Maciuk Sergej,
Orr David,
Rathouská Lucie,
Redmond Joanna M.,
Wilson Peter G.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601584
Subject(s) - reactivity (psychology) , block (permutation group theory) , coupling (piping) , modular design , component (thermodynamics) , chemistry , coupling reaction , polymer chemistry , combinatorial chemistry , catalysis , computer science , organic chemistry , materials science , mathematics , composite material , operating system , physics , medicine , geometry , alternative medicine , pathology , thermodynamics
Palladium‐catalysed coupling reactions based on a novel and easy‐to‐synthesise difluorinated organotrifluoroborate were used to assemble precursors to 6π‐electrocyclisations of three different types. Electrocyclisations took place at temperatures between 90 and 240 °C, depending on the central component of the π‐system; nonaromatic trienes were most reactive, but even systems that required the temporary dearomatisation of two arenyl subunits underwent electrocyclisation, albeit at elevated temperatures. Photochemical conditions were effective for these more demanding reactions. The package of methods delivered a structurally diverse set of fluorinated arenes, spanning a 20 kcal mol −1 range of reactivity, by a flexible route.