Visible-light-induced consecutive C-C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds.

Synthesis of the valuable unsymmetric 1,8-dicarbonyl compounds remains underexplored currently. Herein, we disclose a new strategy for the synthesis of 1,8-diketones through the coupling of cyclopropanols and cyanohydrins under visible-light irradiation. The protocol features a cascade of intriguing ring opening of cyclopropanols and remote cyano migration. The unfavorable addition of an alkyl radical to an electron-rich alkene is facilitated by the intramolecular cyanohydrin interception. A variety of multiply functionalized 1,8-diketones are furnished in useful yields. The products could be further transformed into other valuable compounds, manifesting the utility of this method.

• Publication year

  2019

• Venue

  Chemical Communications

• Publication date

  2019-02-19

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c9cc00378aPMID 30724971
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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