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Updated: May 31, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
One-Pot, Telescoped Aryl Nitrile Synthesis from Benzylic Silyl Ethers
Shohei Hamada1, Suzuka Kubozono2, Kaori Sakamoto2
1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kanazawa 920-1192, Japan.
Abstract:
A one-pot, telescoped transformation of silyl ethers into cyanides that proceeds via silyl-ether oxidation mediated by nitroxyl-radical catalyst 1 and [bis(trifluoroacetoxy)iodo]benzene followed by an imine formation-oxidation sequence using iodine and aqueous ammonia is reported. This transformation is effective for the site-selective transformation of benzylic and allylic silyl ethers in the presence of other silyl ethers. Using an O-protected oxime and a catalytic amount of triflic acid instead of iodine/aqueous ammonia is also effective for cyanation.
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