期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 26, 页码 7653-7657出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703641
关键词
enol ethers; halogen bonding; hypervalent iodine compounds; organocatalysis; umpolung
资金
- MEXT, Japan
- JSPS
- Grants-in-Aid for Scientific Research [17K15423, 15K13757, 16J11381] Funding Source: KAKEN
The umpolung alkylation of silyl enol ethers with an iodonium(III) ylide proceeds under mild conditions to afford various 1,4-dicarbonyl compounds in high yields in the presence of a halogen-bonding catalyst. Unlike typical transition-metal activation processes of such ylide precursors, which tend to proceed via carbenoid intermediates, experimental and computational studies indicate that halogen bonding (XB) between the XB donor catalyst and the iodonium ylide plays a crucial role in promoting the reaction. The identification of a compatible Bronsted base catalyst enabled the extension of this method to enols generated in situ to give the corresponding adducts in good yields.
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