Regioselective Synthesis of Arylsulfonyl Benzophenones via Aerobic Oxidative [3+3] Benzannulation Reactions

Regioselective synthesis of 3‐arylsulfonyl benzophenone derivatives via base mediated, aerial‐oxidative [3+3] benzannulation of α,β‐unsaturated aldehydes and 4‐sulfonyl butenones is reported. A variety of readily available acyclic building blocks are transformed into substituted biaryl ketones in th...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-10, Vol.2020 (40), p.6370-6374
Main Authors: Yadav, Deepak, Joshi, Prabhakar R., Sharma, Sunil K., Menon, Rajeev S.
Format: Article
Language:English
Subjects:
Aerial oxidation
Aldehydes
Benzannulation
Benzophenone
Chemical synthesis
Derivatives
Ketones
Oxidizing agents
Regioselectivity
Substitutes
Sulfones
Terphenyls
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Summary:Regioselective synthesis of 3‐arylsulfonyl benzophenone derivatives via base mediated, aerial‐oxidative [3+3] benzannulation of α,β‐unsaturated aldehydes and 4‐sulfonyl butenones is reported. A variety of readily available acyclic building blocks are transformed into substituted biaryl ketones in this benzannulation reaction. The reaction proceeds under mild conditions in an open flask and uses atmospheric oxygen as oxidant to afford good yields of the products. Analogous benzannulation reactions of chalcone afforded highly substituted m‐terphenyl‐benzophenone derivatives. Regioselective synthesis of sulfonylated benzophenone derivatives through DBU‐mediated, oxidative [3+3] benzannulation reaction of α,β‐unsaturated carbonyl compounds and 4‐sulfonyl butenones has been developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000931