Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones
Lewis acid-enabled reactions of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the Lewis acid and the substituent at N1 of the indoline-2-thiones. With AlCl<sub>3</sub> as the Lewis acid and 1-isopropylindoline-2-thiones as reactants, a direct ring opening with DACs, followed by intramolecular nucleophilic addition/dehydration takes place leading to the formation of dihydro-2<i>H</i>-thiepino[2,3-<i>b</i>]indoles in moderate to good yields. Using Yb(OTf)<sub>3</sub> as promoter and 1-unsubstituted indoline-2-thiones as reactants, a (3 + 2) cycloaddition with DACs accompanied by sulfur rearrangement nucleophilic addition/dehydration takes place to give 3-indolyl-4,5-dihydrothiophenes in moderate yields. In addition, the synthetic transformation of 3-indolyl-4,5-dihydrothiophene to sulfone and indole-based axially chiral scaffolds further extends the synthetic utility and structural complexity.
Authors
- Bo Zhao (ORCID: https://orcid.org/0000-0003-3937-3376)
- Xuelong Wang (ORCID: https://orcid.org/0000-0003-2652-944X)
- Hongjiao Liu
- Bing Zhao (ORCID: https://orcid.org/0000-0003-4140-8072)
- Yan Jiang (ORCID: https://orcid.org/0000-0003-3111-4097)
- Chen-Ying Zhai
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Zhengzhou University (CN)
- Green Chemistry (PL)
- Sichuan University of Science and Engineering (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-20
- DOI
- https://doi.org/10.1021/acs.joc.4c02791
- Citations
- 4
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Department of Science and Technology of Sichuan Province
- Sichuan University of Science and Engineering