Issue 9, 2016

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Research Article
Submitted
18 Jun 2016
Accepted
12 Jul 2016
First published
13 Jul 2016

Org. Chem. Front., 2016,3, 1105-1110

Author version available

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

X. Zhang, J. Liu, Y. Yang, F. Wang, H. Jiang and B. Yin, Org. Chem. Front., 2016, 3, 1105 DOI: 10.1039/C6QO00277C

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