Thiazolium salt-catalyzed C-C triple bond cleavage for accessing substituted 1-naphthols via benzannulation

The first thiazolium salt-catalyzed C-C triple bond cleavage of benzene-linked allene-ynes has been established. The reaction pathway involves [2+2] cycloaddition and ring-opening of in situ generated cyclobutenes with H2O under mild and convenient conditions, and provides practical access to substi...

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Published inChemical communications (Cambridge, England) Vol. 54; no. 2; pp. 164 - 167
Main Authors Zhou, Peng, Wang, Jia-Yin, Zhang, Tian-Shu, Li, Guigen, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2018
Royal Society of Chemistry
Subjects
Allene
Benzene
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Cleavage
Cycloaddition
Physical Sciences
Science & Technology
Substitutes
INTRAMOLECULAR 2+2 CYCLOADDITION
N-HETEROCYCLIC CARBENE
TO-TAIL DIMERIZATION
ALKYNE METATHESIS
VINYLIDENECYCLOPROPANES
EFFICIENT SYNTHESIS
CHEMISTRY
METAL
OXIDATIVE CLEAVAGE
MOLECULAR-OXYGEN
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Summary:The first thiazolium salt-catalyzed C-C triple bond cleavage of benzene-linked allene-ynes has been established. The reaction pathway involves [2+2] cycloaddition and ring-opening of in situ generated cyclobutenes with H2O under mild and convenient conditions, and provides practical access to substituted 1-naphthols with potentially valuable applications.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc08792f