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The direct trifluoromethylsilylation and cyanosilylation of aldehydes via an electrochemically induced intramolecular pathway

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Abstract

The initiator-free electrochemical trifluoromethylsilylation and cyanosilylation of aldehydes were developed in an undivided cell. A DFT study reveals that the direct cathodic activation of trimethylsilyl reagents significantly released the congestion around the ‘Si’ atom, allowing the Si–O bond affinity to form concerted anion intermediates with aldehydes. Thus, intramolecular –CF3 and –CN migration make the reactions much easier to carry out without initiators.

Graphical abstract: The direct trifluoromethylsilylation and cyanosilylation of aldehydes via an electrochemically induced intramolecular pathway

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Article information


Submitted
18 Nov 2019
Accepted
15 Jan 2020
First published
15 Jan 2020

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

The direct trifluoromethylsilylation and cyanosilylation of aldehydes via an electrochemically induced intramolecular pathway

H. Yang, Y. Shen, Z. Xiao, C. Liu, K. Yuan and Y. Ding, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08975F

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