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Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst.

ABSTRACT: An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C-C bond-forming reaction with imines. The process is highly selective, metal-free, and does not require a large excess of the alkylating reagent or the use of acidic additives.

SUBMITTER: Patel NR

PROVIDER: S-EPMC5369175 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst.

Patel Niki R NR Kelly Christopher B CB Siegenfeld Allison P AP Molander Gary A GA

ACS catalysis 20170206 3

An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C-C bond-forming reaction with imines. The process is highly selective, metal-free, and does not require a large excess of the alkylating reagent or the use of acidic additives. ...[more]

PMID: 28367354

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