Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins

Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins

A Pd-catalyzed domino process involving a double norbornene insertion/annulation reaction was developed for the expeditious synthesis of overcrowded olefins. In this one-pot reaction, four new C–C bond formations were achieved by three consecutive Heck carbopalladations and C–H activation across the...

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Veröffentlicht in:Organic letters 2019-06, Vol.21 (11), p.4350-4354
Hauptverfasser: Naveen, Kanagaraj, Perumal, Paramasivan Thirumalai, Cho, Deug-Hee
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container_issue 11
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container_title Organic letters
container_volume 21
creator Naveen, Kanagaraj
Perumal, Paramasivan Thirumalai
Cho, Deug-Hee
description A Pd-catalyzed domino process involving a double norbornene insertion/annulation reaction was developed for the expeditious synthesis of overcrowded olefins. In this one-pot reaction, four new C–C bond formations were achieved by three consecutive Heck carbopalladations and C–H activation across the CC triple bond of 2-alkynyl bromobenzenes with two norbornene rings via a reactive vinylic-Pd­(II) species. This protocol provides a step-economical synthetic system to access the structurally identical molecular machine motifs of overcrowded olefins with high yields.
doi_str_mv 10.1021/acs.orglett.9b01543
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title Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins
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