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Late-Stage N-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis.

ABSTRACT: The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of various trialkylamines. Our catalytic system shows exclusive N-Me selectivity with a wide range of trialkylamines under mild conditions, even in the context of late-stage arylation of pharmaceutical compounds bearing this common structural motif. Mechanistic studies indicate the unconventional behavior of Ni catalyst upon intercepting the α-amino radicals, in which only the primary α-amino radical undergoes a successful cross-coupling process.

SUBMITTER: Shen Y

PROVIDER: S-EPMC8862118 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Late-Stage <i>N</i>-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis.

Shen Yangyang Y Rovis Tomislav T

Journal of the American Chemical Society 20210930 40

The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of various trialkylamines. Our catalytic system shows exclusive <i>N</i>-Me selectivity with a wide range of trialkylamines under mild conditions, even in the context of late-stage arylation of pharmaceutical compounds bearing this common structural motif. Mechan ...[more]

PMID: 34590864

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