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B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

ABSTRACT: An efficient method for the coupling of N-alkylamines with silicon enolates to generate ?-amino carbonyl compounds is disclosed. These reactions proceed by activation of ?-amino C-H bonds by B(C6F5)3, which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.

SUBMITTER: Chan JZ

PROVIDER: S-EPMC6591580 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

Chan Jessica Z JZ Chang Yejin Y Wasa Masayuki M

Organic letters 20190129 4

An efficient method for the coupling of N-alkylamines with silicon enolates to generate β-amino carbonyl compounds is disclosed. These reactions proceed by activation of α-amino C-H bonds by B(C6F5)3, which likely generates a "frustrated" acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of ...[more]

PMID: 30693779

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