4.7 Article

Iodide-Catalyzed Halocyclization/Cycloaddition/Elimination Cascade Reaction

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 6, Pages 2751-2756

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo302676g

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Funding

  1. DFG [NA 955/1-1]
  2. Fonds der Chemischen Industrie (Sachkostenzuschuss)

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An iodocyclization reaction of o-alkynylphenyl carboxaldehydes is reported that is truly catalytic with respect to the electrophilic iodine source. With a combination of tetrabutylammonium iodide (TBAI), Oxone as non-nucleophilic and easy to handle co-oxidant, and fluorinated protic solvents, highly substituted 1-naphthalenones could be prepared in high yields of up to 91%.

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