Butylhydroperoxide mediated radical cyanoalkylation/cyanoalkenylation of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s

A novel sustainable methodology based on one-pot cyanoalkylation/cyanoalkenylation of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s involving a three-component radical cascade pathway has been achieved. Here, tert -butylhydroperoxide (TBHP) acts as an effi...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 21; no. 46; pp. 9255 - 9269
Main Authors Bhuyan, Mayurakhi, Sharma, Suraj, Dutta, Nibedita Baruah, Baishya, Gakul
Format Journal Article
Published 29.11.2023
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Summary:A novel sustainable methodology based on one-pot cyanoalkylation/cyanoalkenylation of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s involving a three-component radical cascade pathway has been achieved. Here, tert -butylhydroperoxide (TBHP) acts as an efficient oxidant, and it smoothly drives the reaction, producing the three-component products in very good to excellent yields. This cascade reaction eliminates the use of any base, additive, metal and hazardous cyanating agent. Additionally, this protocol exclusively delivers a stereospecific product in the case of arylalkynes. The involvement of radicals is evidenced through various radical trapping experiments. We disclosed a TBHP mediated cyanoalkylation/cyanoalkenylation reaction of 2-anilino-1,4-naphthoquinones with vinylarenes/arylalkynes and azobis(alkylcarbonitrile)s in a one-pot three-component fashion via a radical cascade pathway.
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Electronic supplementary information (ESI) available: Experimental data
13
https://doi.org/10.1039/d3ob01528a
C NMR spectra of all compounds, NOE and HRMS analysis. See DOI
H and
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01528a