A simple and efficient protocol was developed for the preparation of challenging α-aryl primary amides. This metal-free coupling process was triggered by TfOH-promoted electrophilic activation of α-silyl nitrile to generate keteniminium ion species, followed by reaction with aryl sulfoxide through [3,3]-sigmatrophic rearrangement to provide the target product. To the best of our knowledge, α-silyl nitrile has been rarely used as a pro-electrophilic reagent. Computational investigations confirmed the transient existence of a highly electrophilic keteniminium intermediate.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Luo, F. (Contributor), Zhou, H. (Contributor), Chen, X. (Contributor), Liu, X. (Contributor), Chen, X. (Contributor), Qian, P. (Contributor), Wu, X. (Contributor), Wang, W. (Contributor) & Zhang, S. (Contributor), Cambridge Crystallographic Data Centre, 2022