Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing <i>S</i>-Heteroaryl Thiocarbamates
Newman-Kwart rearrangement (NKR) is a useful method for synthesizing <i>S</i>-aryl thiocarbamates from <i>O</i>-aryl thiocarbamates. Harsh temperature conditions are required, however, leading to substrate degradation and side reactions. Moreover, reactions using heteroaromatic substrates are quite rare. Herein, we report Bi(OTf)<sub>3</sub>-catalyzed NKR using heteroaromatic substrates under ambient temperature conditions. The reaction extended to not only aza-arene substrates but also thiophene substrates.
Authors
- Tetsuhiro Nemoto (ORCID: https://orcid.org/0000-0001-8858-161X)
- Yuma Okuda
- Keita Yamazaki (ORCID: https://orcid.org/0000-0002-0882-4966)
Institutions
- Chiba University (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-20
- DOI
- https://doi.org/10.1021/acs.joc.4c02728
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Sumitomo Foundation
- Japan Society for the Promotion of Science