Visible-Light/Copper-Catalyzed Three-Component Synthesis of Unprotected β-Arylethylamines and β-Aryl Isothiocyanates via Thianthrenium Salts
Unprotected β-arylethylamines and their derivatives serve as prominently featured structural units in biological molecules. However, most of the reactions reported to date focus on intramolecular and two-component reactions with certain limitations. There is an urgent need for an efficient strategy with a wider range of substrates compared to those of previous methods. Herein, a visible-light-promoted three-component reaction of arylthianthrenium salts, NH<sub>4</sub>SCN, and alkenes is reported using (<i>rac</i>-BINAP)Cu(MeCN)BF<sub>4</sub> as a photoredox catalyst, which yields unprotected β-arylethylamines in the presence of a base, while β-aryl isothiocyanates are unexpectedly obtained under base-free conditions. Moreover, this protocol demonstrates broad substrate generality and a high functional group compatibility.
Authors
- Daoshan Yang (ORCID: https://orcid.org/0000-0002-3047-5416)
- Qilong Wu (ORCID: https://orcid.org/0000-0002-7044-6003)
- Xufeng Li (ORCID: https://orcid.org/0000-0001-8410-1711)
- Hao Xu (ORCID: https://orcid.org/0000-0002-6069-3246)
- Yuqing Zhao (ORCID: https://orcid.org/0000-0002-8359-4830)
- Yongjia Shi
- Jian Lv (ORCID: https://orcid.org/0000-0001-7641-5411)
Institutions
- Qingdao University of Science and Technology (CN)
- Nanjing Forestry University (CN)
- Zhejiang Medicine (China) (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-10
- DOI
- https://doi.org/10.1021/acs.orglett.5c02985
- Citations
- 3
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Taishan Scholar Project of Shandong Province