Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Information
3.2. General Procedure for the Preparation of Selenides 3a–g and 7
3.3. General Procedure for the Preparation of Selenides 5, 6, 9a–c, and 10
3.4. Characterization Data of Products 3a–g, 5, 6, 9a–c and 10
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 | Iodine Source (Equiv) | Solvent (mL) | Time, h | T, °C | Yield, % ** | Se Conversion, % |
---|---|---|---|---|---|---|
1 | 1.0 I2 | MeCN:MeOH (1:0.1) | 40 | 25 | 71 | 54 |
2 | 1.0 I2 | MeOH (1) | 40 | 25 | 90 | 68 |
3 | 1.0 I2 | MeOH (1) | 120 | 25 | 97 | 88 |
4 | 1.5 I2 | MeOH (1) | 40 | 25 | 85 | 86 |
5 | 2.0 I2 | MeOH (1) | 40 | 25 | 87 | ~100 |
6 | 2.0 I2 | MeOH (1) | 20 | 25 | 88 | 69 |
7 | 1.0 I2 | MeOH (1) | 10 | 50 | 70 | 48 |
8 | 2.0 NIS | MeOH (1) | 20 | 25 | 70 | 63 |
9 | 0.2 I2 | DMSO:MeOH (0.15:0.1) | 20 | 25 | Mixture of adducts | 27 |
10 | 2.0 I2 | MeOH (0.2) (5 equiv) | 40 | 25 | 79 | 57 |
11 | – | MeOH (1) | 40 | 25 | 0 | 0 |
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Kurkutov, E.O.; Shainyan, B.A. Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium. Molecules 2022, 27, 6169. https://doi.org/10.3390/molecules27196169
Kurkutov EO, Shainyan BA. Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium. Molecules. 2022; 27(19):6169. https://doi.org/10.3390/molecules27196169
Chicago/Turabian StyleKurkutov, Evgeny O., and Bagrat A. Shainyan. 2022. "Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium" Molecules 27, no. 19: 6169. https://doi.org/10.3390/molecules27196169