TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General
3.2. Method
3.2.1. General Procedure for TBD-Catalyzed Cyanation Reactions of Carbonyl Compounds with Methyl Cyanoformate
3.2.2. General Procedure for TBD-Catalyzed Cyanation Reactions of Aldehydes with Acetyl Cyanide
3.2.3. General Procedure for PS-TBD Catalyzed Cyanation Reactions of Carbonyl Compounds with Methyl Cyanoformate
3.3. General Characterization of the Products
4. Conclusions
Supplementary Materials
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds 2a–2j, 4a–4i, 5a–5l are available from the authors.
Entry | Aldehyde(1) | Product | Solvent | Time | Yield (%) a |
---|---|---|---|---|---|
1 | 2a | CH3CN | 2 h | 90 | |
2 | THF | 2 h | 81 | ||
3 | ClCH2CH2Cl | 3 h | 65 | ||
4 | DMF | 3 h | 60 | ||
5 | toluene | 12 h | 35 | ||
6 b | CH3CN | 12 h | 68 | ||
7 | 2b | CH3CN | 12 h | 89 | |
8 | 2c | 4 h | 92 | ||
9 c | 2d | 0.5 h | 70 | ||
10 | 2e | 4 h | 96 | ||
11 | 2f | 4 h | 90 | ||
12 | 2g | 2 h | 85 | ||
13 | 2h | 4 h | 75 | ||
14 | 2i | 4 h | 96 | ||
15 | 2j | 4 h | 89 | ||
16 | 2k | 4 h | 88 |
Entry | Ketone(3) | Product | Time | Yield (%) a |
---|---|---|---|---|
1 | 4a | 4 h | 85 | |
2 | 4b | 1 h | 90 | |
3 | 4c | 1 h | 86 | |
4 | 4d | 1 h | 70 | |
5 b | 4e | 24 h | 33 | |
6 b | 4f | 24 h | 31 | |
7 b | 4g | 24 h | 75 | |
8 | 4h | 6 h | 55 | |
9 b | 4i | 24 h | 38 | |
10 | 4j | 24 h | 0 |
Entry | Aldehyde(1) | Product | Time | Yield (%) a |
---|---|---|---|---|
1 | 5a | 3 h | 80 | |
2 | 5b | 6 h | 91 | |
3 | 5c | 24 h | 94 | |
4 | 5d | 48 h | 67 | |
5 | 5e | 0.5 h | 40 | |
6 | 5f | 3 h | 90 | |
7 | 5g | 3 h | 90 | |
8 | 5h | 3 h | 92 | |
9 | 5i | 6 h | 70 | |
10 | 5j | 6 h | 88 | |
11 | 5k | 6 h | 85 | |
12 | 5l | 6 h | 80 |
Entry | Carbonyl Compounds | Product | Time | Yield (%) a |
---|---|---|---|---|
1 | 2a | 2 h | 90 | |
2 b | 2a | 2 h | 88 | |
3 c | 2a | 2 h | 92 | |
4 d | 2a | 2 h | 88 | |
5 | 2b | 12 h | 73 | |
6 | 2c | 16 h | 86 | |
7 | 2d | 4 h | 94 | |
8 | 2e | 4 h | 98 | |
9 | 2h | 4 h | 90 | |
10 | 2k | 2 h | 78 | |
11 | 2i | 2 h | 82 | |
12 | 4a | 24 h | 24 | |
13 e | 4a | 12 h | 75 | |
14 e | 4b | 24 h | 70 | |
15 e | 4c | 18 h | 76 |
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Matsukawa, S.; Kimura, J.; Yoshioka, M. TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds. Molecules 2016, 21, 1030. https://doi.org/10.3390/molecules21081030
Matsukawa S, Kimura J, Yoshioka M. TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds. Molecules. 2016; 21(8):1030. https://doi.org/10.3390/molecules21081030
Chicago/Turabian StyleMatsukawa, Satoru, Junya Kimura, and Miki Yoshioka. 2016. "TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds" Molecules 21, no. 8: 1030. https://doi.org/10.3390/molecules21081030