We report the detailed background for the discovery and development of the synthesis of homopropargylic azides by the azido-alkynylation 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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10999984 | PMC |
| http://dx.doi.org/10.3762/bjoc.20.64 | DOI Listing |
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