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Updated: Jul 12, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Synthesis of 1,3-Diaminoisoquinoline Derivatives via N-Oxide Intermediates from o-Cyanobenzyl Cyanides

Daisuke Sakamoto1,2, Alessandro Prescimone1, Philippe H M Marliere2

  • 1Department of Chemistry, University of Basel, Mattenstrasse 22, CH-4058 Basel, Switzerland.

The Journal of Organic Chemistry
|July 10, 2026
PubMed

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

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