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research article
SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes
April 3, 2024
We report the detailed background for the discovery and development of the synthesis of homopropargylic azides by the azidoalkynylation of alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in a 29% yield of the desired product. By switching to a radical-polar crossover approach and after optimization, a high yield (72%) of the homopropargylic azide was reached. Full insights are given about the factors that were essential for the success of the optimization process.
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