Original title: Dichotomy in regioselectivity of Pd-catalyzed direct C-H arylation of protected uracils
Authors: Čerňová, Miroslava ; Hocek, Michal
Document type: Papers
Conference/Event: Chemistry of Nucleic Acid Components /15./, Český Krumlov (CZ), 2011-06-05 / 2011-06-10
Year: 2011
Language: eng
Abstract: Uracil bases and nucleosides bearing aryl groups in positions 5 or 6 are an important class of compounds and display wide range of biological activities1. In addition, arylation in position 5 is often used for labeling of nucleotides, oligonucleotides and DNA for applications in bioanalysis or chemical biology2. The 5- or 6-aryluracils can be prepared by heterocyclization or by cross-coupling reactions of halouracils with arylboronic acids or stannanes or metallated uracils with aryl halides. Direct C–H arylation of uracil is an alternative to classical cross-couplings where the preparation of reactive organometallic reagent is avoided. Recently, we have developed regioselective Pd-catalyzed and/or Cu-mediated direct C–H arylations of 1,3-dimethyluracil as a model compound for pyrimidine bases to position C-5 or C-6 3.
Keywords: direct C-H arylation; palladium; pyrimidines; uracils
Project no.: CEZ:AV0Z40550506 (CEP), LC06077 (CEP)
Funding provider: GA MŠk
Host item entry: Chemistry of Nucleic Acid Components. 15th Symposium, ISBN 978-80-86241-37-1

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0198838

Permalink: http://www.nusl.cz/ntk/nusl-55834


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