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Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines

Published Web Location

https://doi.org/10.1021/acs.joc.9b00518
Abstract

We report a new ligation of cyclopropeniminium ions with bioorthogonal phosphines. Cyclopropeniminium scaffolds are sufficiently stable in biological media and, unlike related isomers, react with functionalized phosphines via formal 1,2-addition to a π-system. The ligation can be performed in aqueous solution and is compatible with existing bioorthogonal transformations. Such mutually compatible reactions are useful for multicomponent labeling.

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