Catalyst-Controlled Inter- and Intramolecular Cascade [4 + 2] Annulations via Benzopyrylium Intermediates

Catalyst-Controlled Inter- and Intramolecular Cascade [4 + 2] Annulations via Benzopyrylium Intermediates

We report two types of catalyst-controlled inter- and intramolecular cascade [4 + 2] annulations between diyne-carbonyls and alkenes, Pt­(II)-catalyzed annulation with two alkenes via two benzopyrylium intermediates, and Au­(I)-catalyzed annulation with one alkene via benzopyrylium and quinodimethan...

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Veröffentlicht in:ACS catalysis 2022-11, Vol.12 (22), p.14330-14336
Hauptverfasser: Koshikawa, Takumi, Nogami, Juntaro, Nagashima, Yuki, Tanaka, Ken
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creator Koshikawa, Takumi
Nogami, Juntaro
Nagashima, Yuki
Tanaka, Ken
description We report two types of catalyst-controlled inter- and intramolecular cascade [4 + 2] annulations between diyne-carbonyls and alkenes, Pt­(II)-catalyzed annulation with two alkenes via two benzopyrylium intermediates, and Au­(I)-catalyzed annulation with one alkene via benzopyrylium and quinodimethane intermediates. Additionally, Au­(I)-catalyzed reactions of highly nucleophilic indole-yne-carbonyls with one alkene afford cascade [4 + 2] annulation products in high yields through benzopyrylium and not quinodimethane but carbocation intermediates, the contribution of which is supported by DFT calculations.
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title Catalyst-Controlled Inter- and Intramolecular Cascade [4 + 2] Annulations via Benzopyrylium Intermediates
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