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Aminomethylation of Aryl Halides using ?-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

ABSTRACT: A protocol for the aminomethylation of aryl halides using ?-silylamines via Ni/photoredox dual catalysis is described. The low oxidation potential of these silylated species enables facile single electron transfer (SET) oxidation of the amine followed by rapid desilylation. The resulting ?-amino radicals can be directly funneled into a nickel-mediated cross-coupling cycle with aryl halides. The process accomplishes aminomethylation under remarkably mild conditions and tolerates numerous aryl- and heteroaryl halides with an array of functional groups.

SUBMITTER: Remeur C 

PROVIDER: S-EPMC5771658 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Remeur Camille C   Kelly Christopher B CB   Patel Niki R NR   Molander Gary A GA  

ACS catalysis 20170816 9

A protocol for the aminomethylation of aryl halides using α-silylamines via Ni/photoredox dual catalysis is described. The low oxidation potential of these silylated species enables facile single electron transfer (SET) oxidation of the amine followed by rapid desilylation. The resulting α-amino radicals can be directly funneled into a nickel-mediated cross-coupling cycle with aryl halides. The process accomplishes aminomethylation under remarkably mild conditions and tolerates numerous aryl- an  ...[more]

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