In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles

Abstract

We present a phosphonium-containing catalyst generated in situ from phosphine and tert-butyl acrylate that serves as an unusual Lewis base catalyst. It was applied for the promotion of a remote 1,6-cyanation reaction of p-quinone methides and fuchsones employing trimethylsilyl cyanide as the cyanide source. A diverse range of α-diaryl and α-triaryl acetonitriles was obtained in high yields under mild reaction conditions with low catalyst loading (5 mol%). The practicality and utility of this protocol were demonstrated via the gram-scale preparation and facile elaboration of products. Mechanistic investigations (in situ NMR and ESI-MS analysis) were employed to characterize the active zwitterionic phosphonium intermediate, which was the “true” active catalyst.

Graphical abstract: In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles

Supplementary files

Article information

Article type
Research Article
Submitted
06 Oct 2021
Accepted
09 Nov 2021
First published
11 Nov 2021

Org. Chem. Front., 2022, Advance Article

In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles

J. Tan, Y. Chen, X. Ren, Y. Guo, B. Yi, H. Zhang, G. Gao and T. Wang, Org. Chem. Front., 2022, Advance Article , DOI: 10.1039/D1QO01501J

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