PulseExploreJournal ClubDebatesTrendingResearchersJournals
Instagram
HomeExploreJournal ClubTrending
Synapse
⌘+K
Synapse
May 10, 2026The Journal of Organic Chemistry0 citations

Photoinduced Radical Alkylation of Cyclic Aldimines with Unactivated C(sp 3 )–H Alcohols Enabled by Alcohol-Directed 1,5-Hydrogen Atom Transfer

View Full Paper
JLJ LIUGMGuozheng MaYLYi Liang

Key Points

  • This research aims to develop a mild method for photoinduced radical alkylation of cyclic aldimines using free alcohols.
  • Leverage visible-light-induced activation of free alcohols using phenyliodine bis(trifluoroacetate) (PIFA)
  • Generate alkoxyl radicals via intramolecular 1,5-hydrogen atom transfer (1,5-HAT)
  • Assess the efficiency of remote C(sp3)–H bond functionalization.
  • Efficient alkylation observed, demonstrating excellent regioselectivity.
  • Process maintains high atom economy and operates under mild conditions.
  • Accessible starting materials facilitate practical applications in cyclic aldimine modification.

Abstract

Herein, we report a mild and photoinduced radical alkylation of cyclic aldimines enabled by visible light. By leveraging visible-light-induced phenyliodine bis(trifluoroacetate) (PIFA) activation of free alcohols, this approach generates alkoxyl radicals via intramolecular 1,5-hydrogen atom transfer (1,5-HAT)─a practical and versatile method for remote C(sp3)–H functionalization known for its excellent regioselectivity. These alkoxyl radicals serve as alkylation agents, enabling efficient remote C(sp3)–H bond functionalization between cyclic aldimines and alcohols. The method features accessible starting materials, high atom economy, simple operation, and mild conditions, providing a practical and versatile pathway for the modification of cyclic aldimine derivatives.

Ask AI
Helpful
Bookmark
Share
View Full Paper

Cite This Study

LIU et al. (2026) studied this question.

synapsesocial.com/papers/6a002087c8f74e3340f9b646https://doi.org/10.1021/acs.joc.6c00663
Ask AI
Helpful
Bookmark
Share
View Full Paper