Modular Construction of Fluoroarenes from a New Difluorinated Building Block by Cross-Coupling/Electrocyclisation/Dehydrofluorination Reactions

Autor:	Alan R. Kennedy, Joanna M. Redmond, Peter G. Wilson, David Orr, Jonathan M. Percy, James W. B. Fyfe, Sergej Maciuk, Helena S. Emerson, Lucie Rathouská
Rok vydání:	2016
Předmět:	Coupling 010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element General Chemistry Modular construction 010402 general chemistry Block (periodic table) 01 natural sciences Combinatorial chemistry Catalysis Coupling reaction 0104 chemical sciences chemistry.chemical_compound Organotrifluoroborate Fluorine Organic chemistry Reactivity (chemistry) QD Palladium
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany). 22(34)
ISSN:	1521-3765 0947-6539
Popis:	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 oC, depending on the central component of the π-system; non-aromatic trienes were most reactive, but even systems which required the temporary dearomatisation of two arenyl sub-units 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ed64a7f3f16902a072884707a4f59cef https://pubmed.ncbi.nlm.nih.gov/27415819 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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