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Cascade Skeletal Rearrangement of Gold Carbene Intermediates: Synthesis of Medium‐Sized Pyrimidine‐Fused Benzolactones
Author(s) -
Wang Ali,
Hu Xiaoping,
Xie Xin,
Liu Yuanhong
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.202100572
Subject(s) - carbene , chemistry , moiety , nucleophile , cycloaddition , reactivity (psychology) , pyrimidine , cascade , aryl , cleavage (geology) , ring (chemistry) , stereochemistry , cascade reaction , combinatorial chemistry , catalysis , organic chemistry , medicine , alkyl , alternative medicine , geotechnical engineering , pathology , chromatography , fracture (geology) , engineering
A gold‐catalyzed cyclization/cascade skeletal rearrangement of o ‐cyanophenylalkynones with 3‐amino‐benzo[ d ]‐isoxazoles has been developed, which provides an approach for synthesizing medium‐sized benzolactones. Based on the experimental results, we postulate that the initial nucleophilic attack occurs preferentially at the keto moiety instead of the gold‐carbene. This reactivity initiates an attractive cascade process involving carbene transfer, 1,2‐aryl migration, cycloaddition, ring‐expansion etc. resulting in multiple bonds cleavage of the initial substrates.