Abstract
The reaction of enynals 1, including o-alkynylbenzaldehydes, and carbonyl compounds 2 in the presence of a catalytic amount of AuBr3 in 1,4-dioxane at 100 °C gave the functionalized aromatic compounds 3 in high yields. The AuBr3-catalyzed formal [4 + 2] benzannulation proceeds most probably through the coordination of the triple bond of 1 to AuBr3, the formation of a pyrylium auric ate complex via the nucleophilic addition of the carbonyl oxygen atom, the reverse electron demand-type Diels-Alder addition of the enols, derived from 2, to the auric ate complex, and subsequent dehydration and bond rearrangement. Similarly, the AuBr3-catalyzed reactions of 1 with acetal compounds afforded the corresponding aromatic compounds in good yields.
Original language | English |
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Pages (from-to) | 7458-7459 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 126 |
Issue number | 24 |
DOIs | |
Publication status | Published - 2004 Jun 23 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry