Site-Selective Copper–<i>N</i>-Heterocyclic Carbene-Catalyzed C(sp<sup>2</sup>)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts
This work demonstrates Cu-NHC (NHC = <i>N</i>-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical alkynylation and rare alkynylative C-H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring a "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. Cu-NHC catalysis enables the use of aryl thianthrenium salts as versatile electrophiles for diverse cross-couplings under mild conditions.
Authors
- Yan Guo (ORCID: https://orcid.org/0000-0002-5724-2110)
- Jin Zhang (ORCID: https://orcid.org/0000-0002-6616-7087)
- Ruihong Wang (ORCID: https://orcid.org/0000-0001-8370-0106)
- Hangsheng Yang (ORCID: https://orcid.org/0000-0002-5968-9223)
- Michal Szostak (ORCID: https://orcid.org/0000-0002-9650-9690)
- Li Sun (ORCID: https://orcid.org/0009-0006-6933-5759)
- Gaopeng Zhang (ORCID: https://orcid.org/0000-0003-2138-4974)
Institutions
- Rutgers, The State University of New Jersey (US)
- Catalytic Materials (United States) (US)
- Community Catalyst (US)
- Shaanxi University of Science and Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00875
- Citations
- 4
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Rutgers, The State University of New Jersey
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Education Department of Shaanxi Province
- National Institute of General Medical Sciences