Issue 18, 2020
From the journal:

Organic Chemistry Frontiers

Phosphine-catalyzed conjugate cyanation of β-trifluoromethyl enones: access to α-trifluoromethyl γ-carbonyl nitriles†

Tao Zhou,a   Xin Ji,a   Junliang Zhang*b  and  Lu Liu ORCID logo *ac  

* Corresponding authors

a School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai, 200241, P. R. China
E-mail: lliu@chem.ecnu.edu.cn

b Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China
E-mail: junliangzhang@fudan.edu.cn

c Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, P. R. China

Abstract

Herein, we developed an efficient conjugate cyanation of β-trifluoromethyl enones with TMSCN mediated by phosphine. In this transformation, the key organophosphorus zwitterion, which was generated in situ by mixing organophosphine with methyl acrylate, could enable this transformation as a highly efficient Lewis base catalyst.

Graphical abstract: Phosphine-catalyzed conjugate cyanation of β-trifluoromethyl enones: access to α-trifluoromethyl γ-carbonyl nitriles

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Article information

DOI
https://doi.org/10.1039/D0QO00582G
Article type
Research Article
Submitted
13 May 2020
Accepted
01 Aug 2020
First published
04 Aug 2020

Org. Chem. Front., 2020,7, 2644-2648

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Phosphine-catalyzed conjugate cyanation of β-trifluoromethyl enones: access to α-trifluoromethyl γ-carbonyl nitriles

T. Zhou, X. Ji, J. Zhang and L. Liu, Org. Chem. Front., 2020, 7, 2644 DOI: 10.1039/D0QO00582G

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