SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

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. Beilstein J. Org. Chem. 2024, 20, 701–713. doi:10.3762/bjoc.20.64
Source: Beilstein Journal of Organic Chemistry - Category: Chemistry Authors: Tags: alkyne azide hypervalent iodine photoredox trifluoroborate salt Commentary Source Type: research