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Efficient Synthesis of Arylated Flavones by Site‐Selective Suzuki–Miyaura Cross‐Coupling Reactions of the Bis(triflate) of 5,7‐ and 7,8‐Dihydroxyflavone
Author(s) -
Eleya Nadi,
Malik Imran,
Reimann Sebastian,
Wittler Kai,
Hein Martin,
Patonay Tamás,
Villinger Alexander,
Ludwig Ralf,
Langer Peter
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101491
Subject(s) - chemistry , trifluoromethanesulfonate , flavones , regioselectivity , selectivity , aryl , combinatorial chemistry , coupling reaction , organic chemistry , suzuki reaction , medicinal chemistry , stereochemistry , catalysis , alkyl , chromatography
Suzuki–Miyaura reactions of the bis(triflate) of 5,7‐ and 7,8‐dihydroxyflavone proceed with very good site selectivity in favor of position 7 and allow the synthesis of various arylated flavones. The reaction of 5,7‐dihydroxyflavone with one equivalent of triflic anhydride also proceeds with very good site selectivity in favor of position 7. The subsequent Suzuki–Miyaura reaction of the product allows the synthesis of 7‐aryl‐5‐hydroxyflavones. The regioselectivity is discussed based on DFT calculations.