We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process was key to develop this transformation. A variety of homopropargylic azides possessing electron-rich and -poor aryls, heterocycles or ether substituents could be accessed in 34-84% yield. The products are synthetically useful building blocks that could be easily transformed into pyrroles or bioactive amines.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10498506 | PMC |
| http://dx.doi.org/10.1039/d3sc03309k | DOI Listing |
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SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes.
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Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
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