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温和条件下铜(I)催化的环状二芳基碘鎓盐、叠氮化钠和炔烃的级联反应:三唑并菲啶的高效合成。

Mild Cu(I)-catalyzed cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes: efficient synthesis of triazolophenanthridines.

机构信息

Sun Yat-sen University Cancer Center, State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, 651 Dongfeng East Road, Guangzhou 510060, China.

出版信息

Org Lett. 2014 Nov 7;16(21):5600-3. doi: 10.1021/ol502654a. Epub 2014 Oct 22.

Abstract

Linear iodoniums are widely used as arylating reagents. However, cyclic diaryl idodoniums are ignored despite their potential to initiate dual arylations, atom and step economically. In our current work, a three-component cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes has been successfully achieved under mild conditions, catalyzed by cheap copper species. The regioselectivity associated with unsymmetrical iodoniums was enhanced by installing two methyls ortho and para to the I(III) center. The reaction enables a rapid access to a variety of complex molecules, triazolophenanthridine derivatives.

摘要

线性碘鎓盐被广泛用作芳基化试剂。然而,尽管环状二芳基碘鎓盐具有经济地引发双重芳基化、原子和步骤的潜力,但它们却被忽视了。在我们目前的工作中,在廉价铜物种的催化下,环状二芳基碘鎓盐、叠氮化钠和炔烃的三组分级联反应在温和条件下得以成功实现。通过在 I(III)中心的邻位和对位安装两个甲基,可增强与不对称碘鎓盐相关的区域选择性。该反应可快速获得各种复杂分子,如三唑并菲啶衍生物。

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