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Construction of multiple bonds via a domino reaction of trifluoroacetimidoyl nitriles with in situ generated bis-nucleophiles

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Abstract

A transition-metal-free double addition/double rearrangement domino reaction affording CF3-substituted pyrimidines was developed, which enables the one-pot construction of five new bonds, namely three C–C bonds and two C–N bonds. The keys to achieve this highly efficient reaction include the delicate design of the bis-nucleophiles in situ generated from the dimerization of alkyl nitriles and the use of trifluoroacetimidoyl nitriles containing C[double bond, length as m-dash]N, C[triple bond, length as m-dash]N, and CF3 groups as the reactant. The mechanistic studies by the experiments and DFT calculations reveal that the transformation involves two addition and two unprecedented rearrangement processes.

Graphical abstract: Construction of multiple bonds via a domino reaction of trifluoroacetimidoyl nitriles with in situ generated bis-nucleophiles

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Article information


Submitted
09 Apr 2020
Accepted
11 Jun 2020
First published
12 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Construction of multiple bonds via a domino reaction of trifluoroacetimidoyl nitriles with in situ generated bis-nucleophiles

D. Li, J. Chen, D. Feng, S. Chen, X. Xu, L. Dang and P. Liu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02398A

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