4.8 Article

Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds

Journal

GREEN CHEMISTRY
Volume 20, Issue 19, Pages 4547-4556

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8gc02574f

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Funding

  1. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [2017/23329-9, 2013/18009-4]
  2. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES)

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Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this BrOnsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three -hydroxy and -alkoxy esters/ketones in just 1 h and at room temperature.

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