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

Paul Dingwall, Andreas Greb, Lorène N S Crespin, Ricardo Labes, Biagia Musio, Jian-Siang Poh, Patrick Pasau, David C Blakemore, Steven V Ley

Research output: Contribution to journalArticle

5 Citations (Scopus)
200 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)1-4
JournalChemical Communications
Early online date11 Sep 2018
DOIs
Publication statusEarly online date - 11 Sep 2018

Fingerprint Dive into the research topics of 'C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow'. Together they form a unique fingerprint.

Cite this