Cu(I)-Catalyzed (4+1) Tandem Annulation of Terminal Alkynes with 2-(Tosylmethyl)phenols: Access to 2,3-Disubstituted Benzofurans and Mechanism Insights
An efficient copper-catalyzed (4+1) tandem annulation has been established for the rapid construction of 2,3-disubstituted benzofurans. This method converts terminal alkynes and 2-(tosylmethyl)phenols using a dual-base system, proceeding via the in situ formation of ortho -quinone methides and alkynyl-copper(I) species. Combined density functional theory calculations and control experiments elucidate a mechanism proceeding through 1,4-conjugate addition, intramolecular cyclization, and base-promoted aromatization. This transformation not only provides a novel and efficient route to functionalized benzofuran motifs but also enriches the chemistry of alkynes and o -quinone methides in organic synthesis.
Authors
- Pan‐Lin Shao (ORCID: https://orcid.org/0000-0001-7415-2195)
- Jinxing Jiang (ORCID: https://orcid.org/0000-0003-1817-1054)
- Kun Yuan (ORCID: https://orcid.org/0000-0001-5552-4424)
- Chun‐An Fan (ORCID: https://orcid.org/0000-0003-4837-3394)
- Xu Yan (ORCID: https://orcid.org/0000-0002-3138-5578)
- Yaqin Cui
- Yi Luo (ORCID: https://orcid.org/0000-0003-0007-0394)
- Li Li (ORCID: https://orcid.org/0009-0003-4636-9487)
- Wenbo Zhang
- Peng Wang
- Yanzhi Liu
Institutions
- Target (United States) (US)
- Institute of Molecular Functional Materials (CN)
- State Key Laboratory of Respiratory Disease (CN)
- State Key Laboratory of Chemical Engineering (CN)
- Tianshui Normal University (CN)
- Lanzhou University (CN)
- Guangzhou Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-06-18
- DOI
- https://doi.org/10.1021/acs.joc.6c00215
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00