Journal
ACS COMBINATORIAL SCIENCE
Volume 21, Issue 8, Pages 588-597Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.9b00076
Keywords
amino acids; decarboxylative coupling; DNA; nickel catalysis; photoredox catalysis
Funding
- Pfizer Inc.
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A new catalytic manifold that merges photoredox with nickel catalysis in aqueous solution is presented. Specifically, the combination of a highly active, yet air-stable, nickel precatalyst with a new electron-deficient pyridyl carboxamidine ligand was key to the development of a water-compatible nickel catalysis platform, which is a crucial requirement for the preparation of DNA-encoded libraries (DELs). Together with an iridium-based photocatalyst and a powerful light source, this dual catalysis approach enabled the efficient decarboxylative arylation of alpha-amino acids with DNA-tagged aryl halides. This C(sp(2))-C(sp(3)) coupling tolerates a wide variety of functional groups on both the amino acid and the aryl halide substrates. Due to the mild and DNA-compatible reaction conditions, the presented transformation holds great potential for the construction of DELs. This was further evidenced by showing that well plate-compatible LED arrays can serve as competent light sources to facilitate parallel synthesis. Lastly, we demonstrate that this procedure can serve as a blueprint toward the adaptation of other established nickel metallaphotoredox transformations to the idiosyncratic requirements of a DEL.
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