A photoinduced arene-alkyne [3+2] cycloaddition cascade of 1-alkynylnaphthalen-2-ols for tunable synthesis of skeletally diverse bridged hexacycles

Photoinduced arene-alkyne [3 + 2] cycloaddition cascades of 1-alkynylnaphthalen-2-ols without a photosensitizer were developed for the first time, enabling tunable synthesis of skeletally diverse bridged hexacyclic architectures with good yields and complete stereoselectivities through solvent-depen...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 9; pp. 1952 - 1958
Main Authors Zhu, Chi-Fan, Zhang, Jie, Zhu, Yi-Long, Hao, Wen-Juan, Tu, Shu-Jiang, Wang, De-Cai, Jiang, Bo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.05.2021
Royal Society of Chemistry
Subjects
Alkynes
Chemistry
Chemistry, Organic
Crystallography
Cycloaddition
Dimethylformamide
Divergence
Organic chemistry
Physical Sciences
Science & Technology
Stereoselectivity
Synthesis
Tetrahydrofuran
ALDOL-LACTONIZATION
DIASTEREOSELECTIVE SYNTHESIS
ACIDS
LIGHT PHOTOREDOX CATALYSIS
PHOTOCYCLOADDITION REACTIONS
PHOTOCHEMICAL-REACTIONS
BOND-CLEAVAGE
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Summary:Photoinduced arene-alkyne [3 + 2] cycloaddition cascades of 1-alkynylnaphthalen-2-ols without a photosensitizer were developed for the first time, enabling tunable synthesis of skeletally diverse bridged hexacyclic architectures with good yields and complete stereoselectivities through solvent-dependent divergent dearomatized cyclodimerizations. The photocatalysis in N,N-dimethylformamide (DMF) delivered functionalized bicyclo[3.2.1]octane-containing bridged oxa-heterocycles, whereas tetrahydrofuran (THF) oriented high stereoselectivity to offer bridged carbocycles. The reaction pathway generates two classes of complex three-dimensional structures that evolve from the same planar internal alkynes.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo00124h