Issue 1, 2018

Utilization of fluoroform for difluoromethylation in continuous flow: a concise synthesis of α-difluoromethyl-amino acids

Abstract

Fluoroform (CHF3) can be considered as an ideal reagent for difluoromethylation reactions. However, due to the low reactivity of fluoroform, only very few applications have been reported so far. Herein we report a continuous flow difluoromethylation protocol on sp3 carbons employing fluoroform as a reagent. The protocol is applicable for the direct Cα-difluoromethylation of protected α-amino acids, and enables a highly atom efficient synthesis of the active pharmaceutical ingredient eflornithine.

Graphical abstract: Utilization of fluoroform for difluoromethylation in continuous flow: a concise synthesis of α-difluoromethyl-amino acids

Supplementary files

Article information

Article type
Communication
Submitted
26 Sep 2017
Accepted
30 Oct 2017
First published
30 Oct 2017
This article is Open Access
Creative Commons BY license

Green Chem., 2018,20, 108-112

Utilization of fluoroform for difluoromethylation in continuous flow: a concise synthesis of α-difluoromethyl-amino acids

M. Köckinger, T. Ciaglia, M. Bersier, P. Hanselmann, B. Gutmann and C. O. Kappe, Green Chem., 2018, 20, 108 DOI: 10.1039/C7GC02913F

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