PulseExploreJournal ClubDebatesTrendingResearchersJournals
Instagram
HomeExploreJournal ClubTrending
Synapse
⌘+K
Synapse
April 17, 2026The Journal of Organic Chemistry3 citations

Visible-Light-Driven Sulfonylation/Cyclization of 1,5-Enynes with Sulfonyl Chlorides via Catalytic TBAI EDA Complexes: Access to 4-Cyano-1-sulfonyl Naphthalenes

View Full Paper
CLChunbo LiLLLei LiYJYongxin Jiang

Key Points

  • The aim is to develop a photocatalytic method for the selective radical cyclization of 1,5-enynes to create naphthalene derivatives.
  • Utilized a metal-free catalytic approach with TBAI to form EDA complexes.
  • Achieved cyclization through 6-endo or 5-exo-trig pathways.
  • Conducted in a one-pot transformation allowing for simultaneous reactions.
  • Successfully synthesized 4-cyano-1-sulfonyl naphthalenes using sulfonyl chlorides.
  • Showed broad substrate scope and excellent tolerance for various functional groups.
  • Demonstrated efficient formation of both C-S and C-C bonds.

Abstract

A metal-free photocatalytic method achieves the selective radical cyclization of 1,5-enynes to construct naphthalene skeletons. This method utilizes an in situ-formed electron donor-acceptor (EDA) complex between sulfonyl chlorides and catalytic TBAI, delivering 4-cyano-1-sulfonyl naphthalenes through a 6-endo cyclization or a 5-exo-trig addition/3-exo-trig cyclization/ring expansion sequence. This one-pot transformation exhibits broad substrate scope and excellent functional group tolerance, efficiently forging both C-S and C-C bonds.

Ask AI
Helpful
Bookmark
Share
View Full Paper

Cite This Study

Li et al. (2026) studied this question.

synapsesocial.com/papers/69e1cdc45cdc762e9d857088https://doi.org/10.1021/acs.joc.6c00403
Ask AI
Helpful
Bookmark
Share
View Full Paper