期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 20, 页码 5288-5297出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201806083
关键词
annulation; carbenes; chemoselectivity; gold; ynamides
资金
- Ministry of Science and Technology [107-3017-F-007-002] Funding Source: Medline
- Ministry of Education [106N506CE1] Funding Source: Medline
Gold-catalyzed annulation of N-propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N-propargyl ynamide, its resulting -imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3-b]quinoline derivative after treatment with p-toluenesulfonic acid. For an internal alkyne, its -imino gold carbene reacts with a tethered alkyne via either a vinyl cation or an alkenylgold carbene; both paths ultimately lead to a 4-ketone-2-aminopyrrole derivative. Our mechanistic analysis indicates that water is a better nucleophile than anthranil for terminal ynamides, whereas water and anthranils are equally reactive for internal ynamides.
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