Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. General Procedure for the Synthesis of Substrates 1a–1w
3.3. General Procedure for the Synthesis of Compounds 3a–3w
3.4. General Procedure for the Synthesis of Ligands L1, L2, and L4
3.5. Characterization of the Products
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Entry | Catalyst (3 mol%) | Ligand (20 mol%) | Solvent | Temp (°C) | Yield (%) b |
---|---|---|---|---|---|
1 | [Rh(Cp*)Cl2]2 | L1 | TFE | 80 | 30 |
2 | [Rh(Cp*)Cl2]2 | L1 | DCE | 60 | 20 |
3 | [Rh(Cp*)Cl2]2 | L1 | t–amyl–OH | 60 | 50 |
4 | [Rh(Cp*)Cl2]2 | L1 | TFE+DCE | 60 | 15 |
5 | [Rh(Cp*)Cl2]2 | L1 | TFT | 60 | 35 |
6 | [Rh(Cp*)Cl2]2 | L1 | t–BuOH | 60 | 55 |
7 | [Rh(Cp*)Cl2]2 | L2 | t–BuOH | 60 | 50 |
8 | [Rh(Cp*)Cl2]2 | L3 | t–BuOH | 60 | 43 |
9 | [Rh(Cp*)Cl2]2 | L4 | t–BuOH | 60 | 75 |
10 | [Rh(Cp*)Cl2]2 | No ligand | t–BuOH | 60 | Trace |
11 | [Ir(Cp*)Cl2]2 | L4 | t–BuOH | 60 | n.d |
12 | [Co(Cp*)(CO)I2]2 | L4 | t–BuOH | 60 | n.d |
13 | [Ru(p–cymene)Cl2]2 | L4 | t–BuOH | 60 | 55 |
14 | [Rh(Cp*)Cl2]2 | AcOH | t–BuOH | 60 | 23 c |
15 | [Rh(Cp*)Cl2]2 | Piv-OH | t–BuOH | 60 | 39 c |
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Kondalarao, K.; Sau, S.; Sahoo, A.K. Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines. Molecules 2023, 28, 5014. https://doi.org/10.3390/molecules28135014
Kondalarao K, Sau S, Sahoo AK. Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines. Molecules. 2023; 28(13):5014. https://doi.org/10.3390/molecules28135014
Chicago/Turabian StyleKondalarao, Koneti, Somratan Sau, and Akhila K. Sahoo. 2023. "Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines" Molecules 28, no. 13: 5014. https://doi.org/10.3390/molecules28135014