4.7 Article

Visible-Light-Driven Epoxyacylation and Hydroacylation of Olefins Using Methylene Blue/Persulfate System in Water

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 8331-8340

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01026

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Funding

  1. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP, Sao Paulo, Brazil) [FAPESP 2017/18400-6]
  2. Faepex-UNICAMP [FAPESP 2017/18400-6]

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A visible-light-driven strategy for hydroacylation and epoxyacylation of olefins in water using methylene blue as photoredox catalyst and persulfate as oxidant is reported. In this unprecedented unified approach, two different transformations are accomplished using only one set of reagents. The method has a broad scope spanning a range of aromatic and aliphatic aldehydes as well as conjugated and nonconjugated olefins to deliver ketones and epoxyketones from abundant and inexpensive chemical feedstocks.

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