Condensation of pyrylium salts with mixed anhydrides: aryl ethers, aryl amines and sterically congested aromatics

The condensation of easily accessible and widely functionalizable 2,4,6-triaryl pyrylium salts with mixed anhydrides, formed in situ from alpha-functionalized sodium acetates and an anhydride solvent, leads in good yields to the corresponding 2,4,6-triaryl benzenes functionalized at their 1-position...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 2; pp. 294 - 298
Main Authors Grabowski, Daniel, Alef, Susanne, Becker, Steven, Mueller, Ute, Schnakenburg, Gregor, Hoeger, Sigurd
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.01.2022
Royal Society of Chemistry
Subjects
Acetic acid
Amines
Anhydrides
Anthracene
Aromatic compounds
Carbazoles
Chemistry
Chemistry, Organic
Condensates
Ethers
Organic chemistry
Photooxidation
Physical Sciences
Salts
Science & Technology
Sodium acetate
Solvents
OLIGOMERS
SHAPE-PERSISTENT MACROCYCLES
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Summary:The condensation of easily accessible and widely functionalizable 2,4,6-triaryl pyrylium salts with mixed anhydrides, formed in situ from alpha-functionalized sodium acetates and an anhydride solvent, leads in good yields to the corresponding 2,4,6-triaryl benzenes functionalized at their 1-position. 4-(Trifluoromethyl)benzoic anhydride has been proven as being the solvent of choice and ortho-disubstituted diphenyl ethers, triphenyl amines and phenyl carbazoles with different functionalizations are synthesized. In addition, sterically hindered anthracene diacetate is condensed with two bis-bromophenyl pyrylium salts which leads after intramolecular Yamamoto coupling to bicyclophanes. In these, the anthracene core is surrounded by phenylenes and protected from photooxidation, leading to a highly stable blue emitting material.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo01419f