Efficiency Enhancement of a Photocatalytic Decarbonylation of an Aminocyclopropenone by Benzothiophene Substitution

To improve the efficiency of the photocatalytic decarbonylation of cyclopropenones, the effects of substituents on cyclopropenone were explored. A benzothiophene-substituted aminocyclopropenone exhibited significantly improved decarbonylation efficiency to produce the corresponding ynamine, which wo...

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Published inJournal of organic chemistry Vol. 86; no. 4; pp. 3625 - 3636
Main Authors Mishiro, Kenji, Nomura, Mitsuki, Furuyama, Taniyuki, Kunishima, Munetaka
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
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Summary:To improve the efficiency of the photocatalytic decarbonylation of cyclopropenones, the effects of substituents on cyclopropenone were explored. A benzothiophene-substituted aminocyclopropenone exhibited significantly improved decarbonylation efficiency to produce the corresponding ynamine, which worked as a potent dehydration condensation agent. The benzothiophene derivative was applicable to the photocatalytic reaction in the presence of potential excited-state quenchers such as oxygen and anilines. The high catalyst sensitivity would be attributed to the involvement of triplet energy transfer reaction pathway, which was not observed in the reaction with previously reported aminocyclopropenones.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02997