期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 355, 期 5, 页码 973-980出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300063
关键词
1; 3-dicarbonyl compounds; palladium; phenols; synergistic catalysis; tertiary amines; TsujiTrost allylation
资金
- Grant-in-Aid for Young Scientists (A) [24686092]
- UBE Foundation
- Grants-in-Aid for Scientific Research [24686092] Funding Source: KAKEN
We demonstrate the synergistic catalysis of a silica-supported diaminopalladium complex and a tertiary amine (SiO2/diamine/Pd/NEt2) as well as synthetic scope of the TsujiTrost reaction of 1,3-dicarbonyls, phenols, and carboxylic acids with allyl carbonate and acetates. The synergistic catalysis of SiO2/diamine/Pd/NEt2 exhibited wide applicability and high activity for the TsujiTrost reaction. For example, the reaction of ethyl 3-oxobutanate with allyl methyl carbonate afforded the allylated product in >99% yield at 70 degrees C for 5h. The yield of allylated products was 26% for SiO2/diamine/Pd, without immobilization of the tertiary amine group. In the reaction of 1.0mmol of ethyl 3-oxobutanate using 0.60mol of Pd in SiO2/diamine/Pd/NEt2, the turnover number (TON) of Pd reached up to 1070 within 24h. Phenols with electron-withdrawing groups, such as nitro and chloro groups, on the para position resulted in high product yields. The SiO2/diamine/Pd/NEt2 catalyst was reusable at least 4 times without appreciable loss of its activity and selectivity in the reaction of p-chlorophenol.
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