Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media
Abstract
:1. Introduction
2. Results and Discussion
Catalyst (mol%) | Solvent | 3a (%) | |
---|---|---|---|
1 | 18-C-6 (1) | CH2Cl2:H2O | 20 |
2 | 18-C-6 (5) | CH2Cl2:H2O | 90a |
3 | 18-C-6 (10) | CH2Cl2:H2O | 94 |
4 | 18-C-6 (10) | CH2Cl2 | 15 |
5 | 18-C-6 (10) | H2O | 80 a |
6 | 15-C-5 (10) | CH2Cl2:H2O | 12 |
7 | - | CH2Cl2:H2O | 7 |
RCHO | Product | Yield (%) | |||
---|---|---|---|---|---|
1 | 1a | 3a | 94 | ||
2 | 1b | 3b | 82 | ||
3 | 1c | 3c | 80 | ||
4 | 1d | 3d | 87 | ||
5 | 1e | 3e | 85 | ||
6 | 1f | 3f | 86 | ||
7 | 1g | 3g | 89 | ||
8 | 1h | 3h | 90 | ||
9 | 1i | 3i | 87 | ||
10 | 1j | 3j | 88 | ||
11 | 1k | 3k | 82 | ||
12 | 1l | 3l | 89 | ||
13 | 1m | 3m | 90 | ||
14 | 1n | 3n | 91 | ||
15 | 1o | 3o | 86 |
3. Experimental
3.1. General
3.2. General Procedure for the Allylation of Aldehydes 1a–o with Potassium Allyltrifluoroborate (2) Catalyzed by 18-C-6
3.3. General Procedure for the Crotylation of 1a with Potassium (E)-crotyltrifluoroborate (4) Catalyzed by 18-C-6
3.4. General Procedure for the Allylation of Compound 6 with Potassium Allyltrifluoroborate (2) Catalyzed by 18-C-6
4. Conclusions
Supplementary Materials
Acknowledgments
References
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Barbosa, F.C.G.; Freitas, J.C.R.; Melo, C.F.; Menezes, P.H.; Oliveira, R.A. Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media. Molecules 2012, 17, 14099-14110. https://doi.org/10.3390/molecules171214099
Barbosa FCG, Freitas JCR, Melo CF, Menezes PH, Oliveira RA. Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media. Molecules. 2012; 17(12):14099-14110. https://doi.org/10.3390/molecules171214099
Chicago/Turabian StyleBarbosa, Fernanda C. G., Juliano C. R. Freitas, Caio F. Melo, Paulo H. Menezes, and Roberta A. Oliveira. 2012. "Allylation of Functionalized Aldehydes by Potassium Allyltrifluoroborate Catalyzed by 18-Crown-6 in Aqueous Media" Molecules 17, no. 12: 14099-14110. https://doi.org/10.3390/molecules171214099