Issue 83, 2018

C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

Abstract

The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C–H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl–alkyl and alkyl–alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.

Graphical abstract: C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

Supplementary files

Article information

Article type
Communication
Submitted
30 Jūl. 2018
Accepted
20 Aug. 2018
First published
11 Sept. 2018
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 11685-11688

C–H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

P. Dingwall, A. Greb, L. N. S. Crespin, R. Labes, B. Musio, J. Poh, P. Pasau, D. C. Blakemore and S. V. Ley, Chem. Commun., 2018, 54, 11685 DOI: 10.1039/C8CC06202A

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