Abstract
2,3-Dibromobenzofuran (1) 2,3,5-tribromobenzofuran (2) undergo regioselective Sonogashira- 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.
Original language | English |
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Pages (from-to) | 1284-1286 |
Number of pages | 3 |
Journal | Synlett |
Issue number | 8 |
DOIs | |
State | Published - 2001 |
Keywords
- Catalysis
- Cross-coupling
- Heterocycles
- Palladium
- Regioselectivity