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Photoredox cross-electrophile coupling in DNA-encoded chemistry
Ist Teil von
Biochemical and biophysical research communications, 2020-12, Vol.533 (2), p.201-208
Ort / Verlag
United States: Elsevier Inc
Erscheinungsjahr
2020
Link zum Volltext
Quelle
MEDLINE
Beschreibungen/Notizen
A catalytic manifold that enables photoredox cross-electrophile coupling of alkyl bromides with DNA-tagged aryl iodides in aqueous solution is presented. This metallaphotoredox transformation was aided by the identification of a new pyridyl bis(carboxamidine) ligand, which proved critical to the nickel catalytic cycle. The described C(sp2)-C(sp3) coupling tolerates a wide range of both DNA-tagged aryl iodides as well as alkyl bromides. Importantly, this reaction was optimized for parallel synthesis, which is a paramount prerequisite for the preparation of combinatorial libraries, by using a 96-well plate-compatible blue LED array as the light source. Therefore, this mild and DNA-compatible transformation is well positioned for the construction of DNA-encoded libraries.
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•Cross-electrophile coupling of alkyl bromides with DNA-tagged aryl iodides.•DNA-compatible C(sp2)-C(sp3) coupling.•Water-compatible nickel-metallaphotoredox catalysis manifold.•96-well plate-compatible blue LED array as light source.