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

Chada Raji Reddy; Muppidi Subbarao; Dattahari H Kolgave; Uprety Ajaykumar; Puthiya Purayil Vinaya

doi:10.1021/acsomega.2c05394

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

ACS Omega. 2022 Oct 10;7(42):38045-38052. doi: 10.1021/acsomega.2c05394. eCollection 2022 Oct 25.

Authors

Chada Raji Reddy¹, Muppidi Subbarao¹, Dattahari H Kolgave¹, Uprety Ajaykumar¹, Puthiya Purayil Vinaya¹

Affiliation

¹ Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.

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.