Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.
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ABSTRACT:
SUBMITTER: Heiss TK
PROVIDER: S-EPMC6758563 | biostudies-literature | 2019 Jun
REPOSITORIES: biostudies-literature
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Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.
Heiss Tyler K TK Prescher Jennifer A JA
The Journal of organic chemistry 20190528 11
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. ...[more]
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