Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones
Abstract
:Introduction
Results and Discussion
| ||||
---|---|---|---|---|
Entry | Phosphines | Aldehyde | solvent | Yield (%) |
1 | TTMPP | C6H5CHO | DMF | 98 |
2 | 4-CH3OC6H4CHO | 99 | ||
3 | 4-ClC6H4CHO | 95 | ||
4 | 4-NO2C6H4CHO | 98 | ||
5 | α-Naphthaldehyde | 92 | ||
6 | β-Naphthaldehyde | 90 | ||
7 | C8H17CHO | 95 | ||
8 | C6H5CH2CH2CHO | 92 | ||
9 | cyclo-C6H11CHO | 93 | ||
10 | TMPP[b] | C6H5CHO | 45 | |
11 | Ph3P | 30 | ||
12 | nBu3P | 68 | ||
13 | TTMPP | THF | 95 | |
14 | CH3CN | 55 | ||
15 | toluene | 30 |
| |||
---|---|---|---|
Entry | Ketones (3) | Temp (°C) | Yield (%) |
1 | | r.t. | 97 |
2[b], [c] | 99 | ||
3 | 95 | ||
4 | 93 | ||
5 | 98 | ||
6 | 90 | ||
7 | 93 | ||
8 | 94 | ||
9 | 76 | ||
10[d] | r.t. | trace | |
11 | 50 °C | 97 | |
12 | 96 | ||
13 | 95 |
| |||
---|---|---|---|
Entry | Carbonyl Compound (3) | Time (h) | Yield (%) |
C6H5CHO | 1 h | 98 | |
2 | 4-CH3OC6H4CHO | 4 h | 85 |
3 | 4-ClC6H4CHO | 95 | |
4 | 4-BrC6H4CHO | 98 | |
5 | 4-NO2C6H4CHO | 88 | |
6 | α-Naphthaldehyde | 1 h | 98 |
7 | β-Naphthaldehyde | 85 | |
8 | C8H17CHO | 4 h | 87 |
9 | C6H5CH2CH2CHO | 92 | |
10 | cyclo-C6H11CHO | 88 | |
11[b] | C6H13COCH3 | 20 h | 75 |
12[b] | C6H5CH2CH2COCH3 | 85 | |
13[b] | C6H5COCH3 | 24 h | 5 |
14[b], [c] | 48 h | 10 |
Experimental
General
General Procedure for the TTMPP-Catalyzed Cyanosilylation of Aldehydes and Ketones
General Procedure for the TTMPP-Catalyzed Cyanocarbonation of Aldehydes
Conclusions
References
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Matsukawa, S.; Sekine, I.; Iitsuka, A. Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones. Molecules 2009, 14, 3353-3359. https://doi.org/10.3390/molecules14093353
Matsukawa S, Sekine I, Iitsuka A. Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones. Molecules. 2009; 14(9):3353-3359. https://doi.org/10.3390/molecules14093353
Chicago/Turabian StyleMatsukawa, Satoru, Izumi Sekine, and Ayumi Iitsuka. 2009. "Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient Catalysts for the Cyanosilylation and Cyanocarbonation of Aldehydes and Ketones" Molecules 14, no. 9: 3353-3359. https://doi.org/10.3390/molecules14093353