Selective Pd-catalyzed α- and β-arylations of the furan rings of (ortho-bromophenyl)furan-2-yl-methanones: C(CO)–C bond cleavage with a furan ring as a leaving group and synthesis of furan-derived fluorenones
Literature Information
Publication Date
2016-07-13
DOI
10.1039/C6QO00277C
Impact Factor
5.281
Authors
Xiaoting Zhang, Jianchao Liu, Yongjie Yang, Furong Wang, Huanfeng Jiang, Biaolin Yin
View Original
Abstract
Selective palladium diacetate-catalyzed α- and β-arylations of the furan rings of (ortho-bromophenyl)furan-2-yl-methanones 1 under two different conditions are reported. In the presence of potassium tert-butoxide as a strong base and triphenylphosphine as a ligand, methanones 1 undergo α-arylation accompanied by C(CO)–C bond cleavage. In contrast, in the presence of potassium carbonate as the base and tricyclohexylphosphonium tetrafluoroborate as the ligand, methanones 1 undergo intramolecular β-arylation to afford furan-derived fluorenones in high yields from a wide variety of substrates. In addition, a one-pot protocol for the successive direct intramolecular β-arylation and intermolecular α-arylation of the furan rings of 1 has been achieved.
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Organic Chemistry Frontiers
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