Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[c]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes

Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[c]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes

A gold‐catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4‐iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6‐endo‐dig diazo‐yne carbocyclization to form the endo...

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Veröffentlicht in:Advanced synthesis & catalysis 2021-08, Vol.363 (16), p.4018-4023
Hauptverfasser: Bao, Ming, Xie, Xiongda, Hu, Wenhao, Xu, Xinfang
Format: Artikel
Sprache:eng
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4-Iminonaphthalenones
Alkyne Carbocyclization
Benzo[c]isoxazoles
Endocyclic Vinyl Carbene
Gold-Catalysis
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container_issue 16
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container_title Advanced synthesis & catalysis
container_volume 363
creator Bao, Ming
Xie, Xiongda
Hu, Wenhao
Xu, Xinfang
description A gold‐catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4‐iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6‐endo‐dig diazo‐yne carbocyclization to form the endocyclic vinyl carbene species from corresponding alkyne‐tethered diazo compounds, followed by electrophilic addition/N−O bond cleavage/aromatization sequence with benzo[c]isoxazoles, which features a C=N bond formation process. In addition, the resulting products could be converted into multi‐substituted 2‐naphthol derivatives in high yields.
doi_str_mv 10.1002/adsc.202100602
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subjects 4-Iminonaphthalenones
Alkyne Carbocyclization
Benzo[c]isoxazoles
Endocyclic Vinyl Carbene
Gold-Catalysis
title Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[c]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes
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