4.8 Article

Alkynylation of Tertiary Cycloalkanols via Radical C-C Bond Cleavage: A Route to Distal Alkynylated Ketones

Journal

ORGANIC LETTERS
Volume 17, Issue 19, Pages 4798-4801

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02353

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Funding

  1. Natural Science Basic Research Plan in Shaanxi Province of China [2014JQ2071]
  2. Fundamental Research Funds of the Central Universities [2015qngz17]

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An efficient Na2S2O8-promoted radical coupling of tertiary cycloalkanols with alkynyl hypervalent iodide reagents via C-C bond cleavage was developed. This tandem ring-opening/alkynylation procedure showed some advantages, including mild conditions and wide substrate scope, thus providing a simple synthetic method for beta-, gamma- and delta-alkynylated ketones.

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