DNA-encoded CH functionality via photoredox-mediated hydrogen atom transformation catalysis. (15th July 2021)

• Record Type: Journal Article
• Authors: Shan, Jinming; Ling, Xing; Liu, JiaXiang; Wang, Xuan; Lu, Xiaojie
• Is Part Of: Bioorganic & medicinal chemistry. Volume 42(2021)
• Publication Date: 2021-07-15
• Subjects: Photoredox -- Hydrogen atom transfer -- N-Boc saturated heterocycle -- DNA Encoded Library (DEL); Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2021.116234
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.