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

Niki R. Patel | Zendy; Christopher B. Kelly | Zendy; Allison P. Siegenfeld | Zendy; Gary A. Molander | Zendy

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

Author(s) -

Niki R. Patel,

Christopher B. Kelly,

Allison P. Siegenfeld,

Gary A. Molander

Publication year - 2017

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.6b03665

Subject(s) - alkylation , reagent , chemistry , alkyl , catalysis , redox , photocatalysis , radical , photoredox catalysis , photochemistry , ammonium , metal , organic chemistry , inorganic chemistry , combinatorial chemistry

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.

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