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Updated: Jun 8, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Visible-light-driven synthesis of alkenyl thiocyanates: novel building blocks for assembly of diverse
Helena F Piedra1, Manuel Plaza1
1Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo Julián Clavería 8 33006 Oviedo Spain plazamanuel@uniovi.es.
Abstract:
The first visible-light-induced protocol for the general preparation of alkenyl thiocyanates from alkenyl bromides is presented. The reaction is simple, proceeds under very mild conditions and demonstrates broad functional group tolerance. Additionally, a flow protocol was developed to enable efficient scale-up of alkenyl thiocyanate synthesis, further enhancing the practicality and value of the method. Importantly, these alkenyl thiocyanates serve as valuable building blocks for the construction of diverse families of sulfur-containing molecules through trifluoromethylations, cycloadditions, oxidations, and C-S or P-S bond forming reactions.
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Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

