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Issue 19, 2018
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Silica-supported HClO4 promotes catalytic solvent- and metal-free O–H insertion reactions with diazo compounds

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Abstract

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 Brønsted 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 α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.

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

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Supplementary files

Article information


Submitted
14 Aug 2018
Accepted
11 Sep 2018
First published
11 Sep 2018

Green Chem., 2018,20, 4547-4556
Article type
Paper

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

R. D. C. Gallo and A. C. B. Burtoloso, Green Chem., 2018, 20, 4547
DOI: 10.1039/C8GC02574F

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