Gold-catalyzed ring enlargement and cycloisomerization of alkynylamide tethered alkylidenecyclopropanes
Alkynylamide tethered alkylidenecyclopropanes 1 undergo gold( i )-catalyzed ring enlargement and cycloisomerization to yield two kinds of heterocyclic polycyclic products 2 and 3 in moderate to good yields depending on the use of different gold( i ) catalysts. The use of PPh 3 AuCl/AgOTf as the cata...
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Veröffentlicht in: | Organic Chemistry Frontiers 2018-10, Vol.5 (20), p.2980-2985 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Alkynylamide tethered alkylidenecyclopropanes
1
undergo gold(
i
)-catalyzed ring enlargement and cycloisomerization to yield two kinds of heterocyclic polycyclic products
2
and
3
in moderate to good yields depending on the use of different gold(
i
) catalysts. The use of PPh
3
AuCl/AgOTf as the catalyst afforded ring enlarged polycyclic products
2
and the use of JohnphosAuCl/NaBARF as the catalyst furnished ring enlarged spiropolycyclic products
3
via
a further intramolecular Friedel–Crafts reaction. A plausible reaction mechanism has also been proposed on the basis of previous literature. Moreover, a useful transformation of ring enlarged spiropolycyclic products
3
to a ring enlarged polycyclic product
4
has also been presented. |
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ISSN: | 2052-4129 2052-4110 2052-4129 2052-4110 |
DOI: | 10.1039/C8QO00907D |