期刊
CHINESE JOURNAL OF ORGANIC CHEMISTRY
卷 39, 期 8, 页码 2328-2332出版社
SCIENCE PRESS
DOI: 10.6023/cjoc201902036
关键词
diazo compounds; alkylidene malonates; rhodium; triphenylarsine; Wittig reaction
资金
- National Natural Science Foundation of China [21432011, 21772224]
- Key Research Program of Frontier Sciences of Chinese Academy of Sciences [QYZDY-SSW-SLH016]
- Strategic Priority Research Program of Chinese Academy of Sciences [XDB20000000]
- Natural Science Foundation of Shanghai City [17ZR1436900]
- Start-up Research Fund of Nanjing Agricultural University [050-804099]
In the presence of triphenylarsine and catalytic amount of Rh-2(OAc)(4), one pot reactions with carbonyl compounds and dimethyl diazomalonate give the corresponding alkylidene and arylidene malonates in moderate to excellent yields (59%similar to 99%). The scope of the carbonyl compounds covered a broad range, including aromatic and aliphatic aldehydes and ketone. The reaction was easily scaled up to gram scale with 0.5 mol% rhodium catalyst loading. The preliminary mechanistic studies showed that the olefination proceeded via a rhodium-carbene transformed arsonium ylide pathway.
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