Download PDF
Synlett 2001; 2001(8): 1284-1286
DOI: 10.1055/s-2001-16052
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

2,3-Disubstituted and 2,3,5-Trisubstituted Benzofurans by Regioselective Pd-Catalyzed Cross-coupling Reactions; a Short Synthesis of Eupomatenoid-15

Thorsten Bach* , Marc Bartels
  • *Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany; Fax + 49(0)89/28 91 33 15; E-mail: thorsten.bach@ch.tum.de
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

2,3-Dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (2) undergo regioselective Sonogashira- and Negishi-type cross-coupling reactions at the 2-position. Subsequent substitution reactions at C-3 are possible for the cross-coupling products obtained from compound 1. A regioselective functionalization of the 3,5-dibromobenzofurans derived from substrate 2 was achieved by an halogen-metal exchange which occurred selectively at the 3-position. In a conclusive reaction step cross-coupling reactions at C-5 were used to build up 2,3,5-trisubstituted benzofurans. As an example, the synthesis of eupomatenoid-15 (8) is described.

catalysis - cross-coupling - heterocycles - palladium - regioselectivity