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

Bioorg Med Chem. 2021 Jul 15:42:116234. doi: 10.1016/j.bmc.2021.116234. Epub 2021 May 28.

Abstract

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.

Keywords: DNA Encoded Library (DEL); Hydrogen atom transfer; N-Boc saturated heterocycle; Photoredox.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamide / chemistry
  • Catalysis
  • DNA / chemistry*
  • Hydrogen / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes

Substances

  • Acrylamide
  • Hydrogen
  • DNA