4.7 Article

Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 11, Pages 7443-7448

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00518

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Funding

  1. U.S. National Institutes of Health [R01 GM126226]
  2. Alfred P. Sloan Foundation

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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 pi-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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