DNA-encoded CH functionality via photoredox-mediated hydrogen atom transformation catalysis

[Display omitted] We described a mode of catalytic activation that accomplished the α-alkylation of N-Boc saturated heterocycles with DNA-linked acrylamide via photoredox-mediated hydrogen atom transfer (HAT) catalysis. This C(sp3)-C(sp3) bond formation reaction tolerated five-, six- and seven-membe...

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Veröffentlicht in:Bioorganic & medicinal chemistry 2021-07, Vol.42, p.116234-116234, Article 116234
Hauptverfasser: Shan, Jinming, Ling, Xing, Liu, JiaXiang, Wang, Xuan, Lu, Xiaojie
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Sprache:eng
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Zusammenfassung:[Display omitted] We described a mode of catalytic activation that accomplished the α-alkylation of N-Boc saturated heterocycles with DNA-linked acrylamide via photoredox-mediated hydrogen atom transfer (HAT) catalysis. This C(sp3)-C(sp3) bond formation reaction tolerated five-, six- and seven-membered cyclic substrates, substantially streamline synthetic efforts to functionalize the α-position of heterocycles with native CH functional handle. This photoredox catalyzed CH functionalization proceeded in mild DNA-compatible condition, and suited for the construction of DNA-encoded libraries.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2021.116234