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

Literature Information

Publication Date 2023-11-10
DOI 10.1039/D3OB01528A
Impact Factor 3.876
Authors

Nibedita Baruah Dutta


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Abstract

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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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