Palladium-Catalyzed\nBicycloaromatization of <i>o</i>‑(Alkynyl)styrenes\nwith Alkynes: Economical Access\nto Chrysene Derivatives

Herein, a palladium-catalyzed bicycloaromatization of <i>o</i>-(alkynyl)styrenes with alkynes is reported. In this protocol,\nthe\n6-<i>endo</i>-<i>dig</i> cyclization of <i>o</i>-(alkynyl)styrenes is followed by deprotonation to complete\nthe first cycloaromatization, and then, a regioselective alkyne insertion/C–H\nactivation occurs to achieve the second cycloaromatization, resulting\nin atom- and step-economical syntheses of polysubstituted chrysenes.\nNotably, the products can be further used to construct π-extended\narenes using the Scholl reaction.

Publication Details

Journal
Figshare
Published
2024-09-30
DOI
https://doi.org/10.1021/acs.orglett.4c03056.s001
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Palladium-Catalyzed\nBicycloaromatization of o‑(Alkynyl)styrenes\nwith Alkynes: Economical Access\nto Chrysene Derivatives

Figshare
Catalytic Alkyne Reactions
article

Palladium-Catalyzed\nBicycloaromatization of o‑(Alkynyl)styrenes\nwith Alkynes: Economical Access\nto Chrysene Derivatives

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Abstract

Herein, a palladium-catalyzed bicycloaromatization of <i>o</i>-(alkynyl)styrenes with alkynes is reported. In this protocol,\nthe\n6-<i>endo</i>-<i>dig</i> cyclization of <i>o</i>-(alkynyl)styrenes is followed by deprotonation to complete\nthe first cycloaromatization, and then, a regioselective alkyne insertion/C–H\nactivation occurs to achieve the second cycloaromatization, resulting\nin atom- and step-economical syntheses of polysubstituted chrysenes.\nNotably, the products can be further used to construct π-extended\narenes using the Scholl reaction.

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Catalytic Alkyne Reactions
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Palladium-Catalyzed\nBicycloaromatization of <i>o</i>‑(Alkynyl)styrenes\nwith Alkynes: Economical Access\nto Chrysene Derivatives · Figshare (2024) | TGRS Research Map | TGRS