4.7 Article

Visible Light-Mediated [2+2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 14, Pages 8948-8958

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00855

Keywords

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Funding

  1. CSIR [P-81-113]
  2. DBT, New Delhi [1151/2016]

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A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

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