Issue 49, 2017

Enabling iron catalyzed Doyle–Kirmse rearrangement reactions with in situ generated diazo compounds

Abstract

Slow addition of sodium nitrite allows the in situ preparation of highly explosive diazo compounds and enables their safe and scalable application in iron catalyzed rearrangement reactions of allylic and propargylic sulfides. With catalyst loadings as low as 0.1 mol% an effective entry into α-mercapto-nitriles, α-mercapto-esters and α-trifluoromethyl-sulfides on a gram-scale is achieved.

Graphical abstract: Enabling iron catalyzed Doyle–Kirmse rearrangement reactions with in situ generated diazo compounds

Supplementary files

Article information

Article type
Communication
Submitted
11 Apr 2017
Accepted
19 May 2017
First published
22 May 2017

Chem. Commun., 2017,53, 6577-6580

Enabling iron catalyzed Doyle–Kirmse rearrangement reactions with in situ generated diazo compounds

K. J. Hock, L. Mertens, R. Hommelsheim, R. Spitzner and R. M. Koenigs, Chem. Commun., 2017, 53, 6577 DOI: 10.1039/C7CC02801F

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