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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.
Jürg Alexander Schiffmann, Soheyl Massoudi, Cyril Picard
Olga Fink, Chao Hu, Sayan Ghosh