期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 18, 页码 13041-13055出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01807
关键词
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资金
- Ruprecht-Karls-Universitat Heidelberg (Heidelberg University)
- BASF SE
The vinylation of various nucleophiles with acetylene is achieved using organocatalysis with easily accessible phosphines. A detailed mechanistic investigation supports a nucleophilic activation of acetylene by the phosphine catalyst. Various organic compounds were successfully synthesized through this method.
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 degrees C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
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