Divergent Synthesis of Benzo[4,5]imidazo[2,1-<i>b</i>][1,3]thiazines and α-Trifluoromethyl-β-arylthio Tertiary Alcohols from 2-Mercaptobenzimidazoles and α-CF<sub>3</sub> Alkenes
An efficient and metal-free approach for the divergent synthesis of 2-fluoro-3-aryl-4<i>H</i>-benzo[4,5]imidazo[2,1-<i>b</i>][1,3]thiazines and <i>α</i>-trifluoromethyl-<i>β</i>-arylthio tertiary alcohols from 2-mercaptoimidazoles and <i>α</i>-CF<sub>3</sub> alkenes has been developed. The chemoselectivity was well controlled by base or light; a series of 2-fluoro-3-aryl-4<i>H</i>-benzo[4,5]imidazo[2,1-<i>b</i>][1,3]thiazines were afforded <i>via</i> base-mediated sequential S<sub>N</sub>2'- and S<sub>N</sub>V-type reactions. Meanwhile, <i>α</i>-trifluoromethyl-<i>β</i>-arylthio tertiary alcohols could be selectively achieved through visible-light-driven and electron donor-acceptor (EDA) complex-initiated radical cascade thiolation/hydroxylation in the absence of base, transition metal, and external photocatalyst.
Authors
- Weiwei Jin (ORCID: https://orcid.org/0000-0002-5996-3229)
- Fei Xue (ORCID: https://orcid.org/0000-0002-9257-5076)
- Chenjiang Liu (ORCID: https://orcid.org/0000-0002-8241-0809)
- Ziren Chen (ORCID: https://orcid.org/0000-0002-3298-9584)
- Bin Wang (ORCID: https://orcid.org/0000-0002-8755-6401)
- Yonghong Zhang (ORCID: https://orcid.org/0000-0002-7740-9408)
- Yu Xia (ORCID: https://orcid.org/0000-0002-0591-9169)
- Hua Kuan Lin
- Shaofeng Wu (ORCID: https://orcid.org/0009-0008-8396-1742)
Institutions
- China Jiliang University (CN)
- Xinjiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c03765
- Citations
- 12
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.50
Funders
- Natural Science Foundation of Xinjiang Province
- Government of Xinjiang Uygur Autonomous Region of China
- National Natural Science Foundation of China