Synthesis of 4‐Formyl‐2‐arylbenzofuran Derivatives by PdCl(C 3 H 5 )dppb‐Catalyzed Tandem Sonogashira Coupling‐Cyclization under Microwave Irradiation ‐ Application to the Synthesis of Viniferifuran Analogues | Zendy

Vo Duy D. | Zendy; Elofsson Mikael | Zendy

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Synthesis of 4‐Formyl‐2‐arylbenzofuran Derivatives by PdCl(C 3 H 5 )dppb‐Catalyzed Tandem Sonogashira Coupling‐Cyclization under Microwave Irradiation ‐ Application to the Synthesis of Viniferifuran Analogues

Author(s) -

Vo Duy D.,

Elofsson Mikael

Publication year - 2017

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201701490

Subject(s) - sonogashira coupling , tandem , catalysis , microwave irradiation , demethylation , chemistry , benzofuran , medicinal chemistry , copper , combinatorial chemistry , photochemistry , palladium , stereochemistry , organic chemistry , materials science , biochemistry , gene expression , dna methylation , composite material , gene

Herein we present the use of low catalyst loading of PdCl(C 3 H 5 )dppb (1 mol%) to directly prepare 4‐CHO‐2‐arylbenzofurans by copper‐free tandem Sonogashira coupling‐cyclization under microwave irradiation. The method was utilized to prepare highly substituted analogues of viniferifuran, a biologically active resveratrol dimer. Key transformations included the application of PdCl(C 3 H 5 )dppb (5 mol%) catalyzed direct arylation of C‐3 sterically congested C‐2 and C‐4 substituted benzofuran substrates. Finally, we demonstrated that BCl 3 /TBAI is superior to BBr 3 for final demethylation.

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