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Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids.

ABSTRACT: An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the presence of potassium persulfate (K₂S₂O₈) as the oxidant. Further, this approach was extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively. The present three-component method offers the diverse substitutions on selenium involving two C-Se and one C-C bond formations.

SUBMITTER: Raji Reddy C

PROVIDER: S-EPMC9608386 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids.

Raji Reddy Chada C Subbarao Muppidi M Kolgave Dattahari H DH Ajaykumar Uprety U Vinaya Puthiya Purayil PP

ACS omega 20221010 42

An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the presence of potassium persulfate (K2S2O8) as the oxidant. Further, this approach was extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding s ...[more]

PMID: 36312410

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