Distinct Selectivity of 2-Aryl Thioquinazolinones in the Sulfur Directing Rh(III)-Catalyzed Amidation Reaction
Sulfur-directed C-H functionalization of N-heterocycles has emerged as an alternative solution to weakly coordinating carbonyl directing groups. In this study, we describe a sulfur-promoted Rh(III)-catalyzed C5 amidation of 4-thioquinazolinones using dioxazolones, yielding 5-amido-4-thioquinazolinones. The synthetic utility was demonstrated through a gram-scale experiment and synthetic modifications of the title compounds. A series of mechanistic investigations, including competition experiments, elucidated the effectiveness of the sulfur directing group in this process.
Authors
- Jeonghyun Min
- Keunju Park
- In Su Kim (ORCID: https://orcid.org/0000-0002-2665-9431)
- Youyoung Kim
- Youngil Lee (ORCID: https://orcid.org/0000-0001-8497-0300)
- Anand Kumar (ORCID: https://orcid.org/0009-0002-8058-8491)
- Neeraj Kumar Mishra (ORCID: https://orcid.org/0000-0002-5562-7519)
- Pargat Singh (ORCID: https://orcid.org/0000-0002-0203-0612)
Institutions
- University of Lucknow (IN)
- University of Ulsan (KR)
- Korea Research Institute of Chemical Technology (KR)
- Sungkyunkwan University (KR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-09
- DOI
- https://doi.org/10.1021/acs.joc.5c00952
- Citations
- 4
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Research Foundation of Korea