4.7 Article

A visible light-mediated three-component strategy based on the ring-opening of cyclic ethers with aryldiazoacetates and nucleophiles

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 5, Pages 1321-1326

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01780b

Keywords

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Funding

  1. CNPq [142474/2018-5]
  2. FAPESP [2020/00144-6, 2018/03910-1, 2020/06536-3, 2019/01235-8]
  3. FAEPEX [2466/20]
  4. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [18/03910-1] Funding Source: FAPESP

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A blue light-promoted reaction has been developed, which allows the incorporation of aryldiazoacetates and different nucleophiles into a single product using THF (and other cyclic ethers) as the solvent. This transformation represents an O-H insertion strategy of complex alcohols into aryldiazoesters without pre-assembling. The method is mild and efficient, and can proceed at room temperature without the need for metals.
A blue light-promoted reaction between aryldiazoacetates and different nucleophiles has been developed in the presence of THF (and other cyclic ethers) as the solvent, allowing the incorporation of these three elements into a single product. Formally, this transformation represents an O-H insertion strategy of more complex alcohols into aryldiazoesters, without the need of pre-assembling them. The method is mild and efficient and proceeds in the absence of metals, generally at room temperature.

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