State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , People's Republic of China.
Org Lett. 2018 Jun 1;20(11):3273-3277. doi: 10.1021/acs.orglett.8b01145. Epub 2018 May 16.
A gold-catalyzed cycloisomerization of ynamide-ynes via a formal dehydro-Diels-Alder reaction has been developed, providing an attractive route to diversely substituted benzo[ b]carbazoles. The reaction likely proceeds via regioselective attack of the pendant alkyne moiety to a keteniminium ion intermediate followed by benzannulation. The method offers several advantages such as high efficiency, mild reaction conditions, and wide functional group tolerance and serves as a highly useful complement to the thermal DDA reactions of ynamide-ynes.
发展了一种通过形式的去氢 Diels-Alder 反应的金催化的酰胺-炔环异构化反应，为各种取代的苯并[b]咔唑提供了一个有吸引力的途径。该反应可能是通过末端炔基部分对烯酮亚胺离子中间体的区域选择性进攻，然后进行苯并环化来进行的。该方法具有高效、温和的反应条件、广泛的官能团容忍度等优点，是酰胺-炔热 DDA 反应的很好补充。
