A metal-free visible-light-promoted phosphorylation/cyclization reaction in water towards 3-phosphorylated benzothiophenes

A metal-free visible-light-induced 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)-catalyzed phosphorylation/cyclization reaction was developed in water at room temperature for the synthesis of 3-phosphorylated benzothiophenes. Notably, the conventional organic solvents were avoided. More...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 14; pp. 1884 - 1889
Main Authors Yuan, Xiao-Ya, Zeng, Fan-Lin, Zhu, Hu-Lin, Liu, Yan, Lv, Qi-Yan, Chen, Xiao-Lan, Peng, Lifen, Yu, Bing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.07.2020
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Functional groups
Light effects
Organic chemistry
Organic solvents
Phosphorylation
Physical Sciences
Room temperature
Science & Technology
Silver
QUINOLINE N-OXIDES
CATALYSIS
THIOLS
ACIDS
AMINES
INDUCED DEOXYGENATIVE C2-SULFONYLATION
EFFICIENT SYNTHESIS
C-H
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Summary:A metal-free visible-light-induced 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)-catalyzed phosphorylation/cyclization reaction was developed in water at room temperature for the synthesis of 3-phosphorylated benzothiophenes. Notably, the conventional organic solvents were avoided. More importantly, this silver-free system circumvents the generation of by-product benzo[b]phosphole oxides. With this strategy, a series of 3-phosphorylated benzothiophenes bearing various functional groups were synthesized in good to excellent yields.
Bibliography:ObjectType-Article-1
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content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d0qo00222d