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

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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

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Publication details

The article was received on 26 Sep 2017, accepted on 30 Oct 2017 and first published on 30 Oct 2017


Article type: Communication
DOI: 10.1039/C7GC02913F
Citation: Green Chem., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C7GC02913F

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