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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
Author(s) -
Bao Ming,
Xie Xiongda,
Hu Wenhao,
Xu Xinfang
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100602
Subject(s) - chemistry , diazo , alkyne , carbene , triple bond , bond cleavage , aromatization , catalysis , electrophile , medicinal chemistry , cyclopropanation , stereochemistry , combinatorial chemistry , double bond , organic chemistry
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.