Visible-Light-Mediated Dual Functionalization of Allenes: Regio- and Stereoselective Synthesis of Vinylsulfone Azides,The Journal of Organic Chemistry

当前位置： X-MOL 学术 › J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Visible-Light-Mediated Dual Functionalization of Allenes: Regio- and Stereoselective Synthesis of Vinylsulfone Azides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-12-20 , DOI: 10.1021/acs.joc.3c02515
Houqi Guo ₁ , Xin Ruan ₁ , Zekun Xu ₁ , Kai Wang _{1,

2} , Xiang Li ₁ , Jun Jiang _{1,

2}

Affiliation

A gentle and effective method for the photocatalytic dual functionalization of allenes with high regio- and stereoselectivity using a nonmetallic catalyst is described. Inexpensive and easily available sulfinates and TMSN₃ were employed as sulfone and azido sources, respectively. The method is characterized by satisfactory substrate compatibility and tolerance toward functional groups. The straightforward initial mechanistic experiments suggested that the reaction could follow a radical pathway. The synthesis of vinylsulfone azide derivatives presented here offers a promising scaffold for the future development of vinyl sulfone-based drugs and functional bioorthogonal reagents.

中文翻译：

可见光介导的丙二烯双官能化：乙烯基砜叠氮化物的区域选择性和立体选择性合成

描述了一种使用非金属催化剂对丙二烯进行光催化双官能化的温和有效的方法，具有高区域和立体选择性。廉价且容易获得的亚磺酸盐和TMSN ₃分别用作砜和叠氮源。该方法的特点是具有良好的底物兼容性和对官能团的耐受性。简单的初始机制实验表明该反应可能遵循激进的途径。这里介绍的乙烯基砜叠氮化物衍生物的合成为乙烯基砜基药物和功能性生物正交试剂的未来发展提供了一个有前景的支架。

更新日期：2023-12-20

点击分享查看原文

点击收藏

阅读更多本刊新发论文