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Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides.

ABSTRACT: A wide range of alkyl-, aryl- and heteroarylzinc halides were aminated with highly functionalized alkyl, aryl, and heterocyclic azides. The reaction proceeds smoothly at 50?°C within 1?h in the presence of FeCl₃ (0.5?equiv) to furnish the corresponding secondary amines in good yields. This method was extended to peptidic azides and provided the arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of pharmaceutical relevance using this iron-mediated electrophilic amination as the key step.

SUBMITTER: Graßl S

PROVIDER: S-EPMC6972526 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides.

Graßl Simon S Singer Johannes J Knochel Paul P

Angewandte Chemie (International ed. in English) 20191119 1

A wide range of alkyl-, aryl- and heteroarylzinc halides were aminated with highly functionalized alkyl, aryl, and heterocyclic azides. The reaction proceeds smoothly at 50 °C within 1 h in the presence of FeCl<sub>3</sub> (0.5 equiv) to furnish the corresponding secondary amines in good yields. This method was extended to peptidic azides and provided the arylated substrates with full retention of configuration. To demonstrate the utility of this reaction, we prepared two amine derivatives of ph ...[more]

PMID: 31599056

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