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

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

Chada Raji Reddy  1 , Muppidi Subbarao  1 , Dattahari H Kolgave  1 , Uprety Ajaykumar  1 , Puthiya Purayil Vinaya  1
Affiliations

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

Chada Raji Reddy et al. ACS Omega. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Selected molecules with spiro-cyclohexadienone framework.
Scheme 1
Scheme 1. Synthetic Strategies to Diverse Seleno-spiro Cyclohexadienones
Scheme 2
Scheme 2. Scope of Boronic Acid and N-Arylpropiolamides
Scheme 3
Scheme 3. Scope of 4-Methoxyphenyl-propiolates
Scheme 4
Scheme 4. Selenylative ipso-Annulation of Biaryl Ynones
Scheme 5
Scheme 5. Synthesis of Selenyl Pyrrolo-[2,1-j]quinolone
Scheme 6
Scheme 6. Control Experiments
Scheme 7
Scheme 7. Probable Reaction Mechanism
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