路易斯酸催化通过脱水[3 + 3]环化反应合成咔唑和萘的串联反应。
Lewis acid catalyzed cascade reaction to carbazoles and naphthalenes via dehydrative [3 + 3]-annulation.
作者信息
Wang Shaoyin, Chai Zhuo, Wei Yun, Zhu Xiancui, Zhou Shuangliu, Wang Shaowu
机构信息
The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University , Wuhu, Anhui 241000, P. R. China.
出版信息
Org Lett. 2014 Jul 3;16(13):3592-5. doi: 10.1021/ol501605h. Epub 2014 Jun 24.
A novel Lewis acid catalyzed dehydrative [3 + 3]-annulation of readily available benzylic alcohols and propargylic alcohols was developed to give polysubstituted carbazoles and naphthalenes in moderate to good yields with water as the only byproduct. The reaction was presumed to proceed via a cascade process involving Friedel-Crafts-type allenylation, 1,5-hydride shift, 6π-eletrocyclization, and Wagner-Meerwein rearrangement.
开发了一种新型的路易斯酸催化的脱水[3 + 3]环化反应，该反应以易得的苄醇和炔丙醇为原料，以水为唯一副产物，以中等到良好的产率得到多取代咔唑和萘。推测该反应通过包括傅克型烯丙基化、1,5-氢迁移、6π-电环化和瓦格纳-米尔温重排的串联过程进行。
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