Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans

An efficient one-pot protocol was developed for the construction of the benzofuran system from aryl halides and protected iodophenols using carbinol-based acetylene sources. The sequence includes alternating palladium-catalyzed Sonogashira couplings and deprotection steps concluded by a ring closure...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 64; no. 37; pp. 8992 - 8996
Main Authors Csékei, Márton, Novák, Zoltán, Kotschy, András
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.09.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
ROUTE
ALKYNYLSILANES
ANALOGS
O-ALKYNYLPHENOLS
PALLADIUM-CATALYZED CYCLIZATION
ARYL HALIDES
EFFICIENT SYNTHESIS
ACTIVATED AROMATICS
VIGNAFURAN
Online AccessGet full text

Cover

More Information
Summary:An efficient one-pot protocol was developed for the construction of the benzofuran system from aryl halides and protected iodophenols using carbinol-based acetylene sources. The sequence includes alternating palladium-catalyzed Sonogashira couplings and deprotection steps concluded by a ring closure. The developed one-pot procedure was compared with the stepwise approach and its efficiency was also demonstrated by the total synthesis of vignafuran, a benzofuran natural product. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.05.100