The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter () was found to correlate to the reaction efficiency, which enabled the formation of C-C and C-C bonds under otherwise identical conditions from structurally dissimilar nucleophiles.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8120647 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.1c01032 | DOI Listing |
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