Issue 19, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Aug 2018
Accepted
11 Sep 2018
First published
11 Sep 2018

Green Chem., 2018,20, 4547-4556

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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