Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates
Abstract
:1. Introduction
2. Results
3. Conclusions
4. Materials and Methods
4.1. General Methods
4.2. General Procedure for Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling
4.3. General Procedure for Determination of Relative Reactivity
4.4. Characterization Data for Starting Materials
4.4.1. Phenyl 4-chlorobenzenesulfonate (1a)
4.4.2. 4-(tert-Butyl)phenyl 4-chlorobenzenesulfonate (1b)
4.4.3. 4-Methoxyphenyl 4-chlorobenzenesulfonate (1c)
4.4.4. 4-Fluorophenyl 4-chlorobenzenesulfonate (1d)
4.4.5. o-Tolyl 4-chlorobenzenesulfonate (1e)
4.4.6. 2,6-Dimethylphenyl 4-chlorobenzenesulfonate (1f)
4.4.7. Naphthalen-2-yl 4-chlorobenzenesulfonate (1g)
4.4.8. 4-Methoxyphenyl 3-chlorobenzenesulfonate (1h)
4.4.9. 4-Methoxyphenyl 2-chlorobenzenesulfonate (1i)
4.5. Characterization Data for Cross-Coupling Products
4.5.1. Phenyl 4-ethylbenzenesulfonate (2a)
4.5.2. 4-(tert-Butyl)phenyl 4-ethylbenzenesulfonate (2b)
4.5.3. 4-Methoxyphenyl 4-ethylbenzenesulfonate (2c)
4.5.4. 4-Fluorophenyl 4-ethylbenzenesulfonate (2d)
4.5.5. o-Tolyl 4-ethylbenzenesulfonate (2e)
4.5.6. 2,6-Dimethylphenyl 4-ethylbenzenesulfonate (2f)
4.5.7. Naphthalen-2-yl 4-ethylbenzenesulfonate (2g)
4.5.8. 4-Methoxyphenyl 3-ethylbenzenesulfonate (2h)
4.5.9. 4-Methoxyphenyl 2-ethylbenzenesulfonate (2i)
4.5.10. 4-Methoxyphenyl 4-cyclohexylbenzenesulfonate (2j)
4.5.11. 4-Methoxyphenyl 4-isopropylbenzenesulfonate (2k)
4.5.12. 4-Methoxyphenyl 4-phenethylbenzenesulfonate (2l)
4.5.13. 4-Methoxyphenyl 4-(2-(1,3-dioxan-2-yl)ethyl)benzenesulfonate (2m)
Supplementary Materials
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Entry | Fe(acac)3 (mol%) | Ligand | mol% | Time | Yield (%) 2 |
---|---|---|---|---|---|
1 | - | - | - | 10 min | 0 |
2 | 5 | - | - | 10 min | 73 |
3 | 5 | DMI | 20 | 10 min | 81 |
4 | 5 | DMI | 50 | 10 min | 87 |
5 | 5 | DMI | 200 | 10 min | 98 |
6 3 | 5 | DMI | 600 | 10 min | >98 |
Entry | Substrate | 2 | Product | Yield (%) |
---|---|---|---|---|
1 | 2a | 98 | ||
2 | 2b | 98 | ||
3 | 2c | 98 | ||
4 | 2d | 95 | ||
5 | 2e | 98 | ||
6 | 2f | 97 | ||
7 2 | 2g | 73 | ||
8 | 2h | 98 | ||
9 3 | 2i | 59 | ||
10 3 | 2j | 98 | ||
11 3 | 2k | 98 | ||
12 4 | 2l | 98 | ||
13 5 | 2m | 98 |
Entry | Fe(acac)3 (mol%) | Ligand | mol% | Time (min) | Yield (%) 2 |
---|---|---|---|---|---|
1 | 5 | 600 | 10 | >98 | |
2 | 5 | 600 | 10 | >98 | |
3 | 5 | 600 | 10 | 94 | |
4 | 5 | 600 | 10 | >98 | |
5 | 5 | 600 | 10 | 97 | |
6 | 5 | 600 | 10 | 78 | |
7 | 5 | 600 | 10 | 94 |
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Bisz, E. Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates. Molecules 2021, 26, 5895. https://doi.org/10.3390/molecules26195895
Bisz E. Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates. Molecules. 2021; 26(19):5895. https://doi.org/10.3390/molecules26195895
Chicago/Turabian StyleBisz, Elwira. 2021. "Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates" Molecules 26, no. 19: 5895. https://doi.org/10.3390/molecules26195895