Department of Chemistry and Chemistry Institute of Functional Materials, Pusan National University , Busan 609-735, Korea.
Org Lett. 2016 May 6;18(9):2204-7. doi: 10.1021/acs.orglett.6b00821. Epub 2016 Apr 20.
A base-controlled Cu-catalyzed tandem cyclization/alkynylation of propargylic amines provides rapid access to functionalized indolizine derivatives under mild reaction conditions. The reaction first proceeded via a 5-endo-dig aminocupration, followed by a coupling between the copper-bound intermediate and alkynyl bromide, to afford the products in good to excellent yields. The successful tandem reaction is attributed to the unique property of the bases, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene used).
在温和的反应条件下，一种基于铜催化的炔丙胺的串联环化/炔基化反应，为功能化的吲哚嗪衍生物提供了快速的合成途径。该反应首先通过 5-endo-dig 氨基铜化反应进行，然后铜结合中间体与炔基溴化物之间进行偶联，以良好至优异的收率得到产物。成功的串联反应归因于碱的独特性质，即 DBU（1,8-二氮杂双环[5.4.0]十一-7-烯）和 MTBD（7-甲基-1,5,7-三氮杂双环[4.4.0]癸-5-烯）的使用。
