Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides

Shengkun Guo; Xiaoyu Shen; Xiaoyun Chen; Huaguang Yu; Ying Han; Chaoguo Yan; Yaocheng Shi; Hong Hou; Shaoqun Zhu

doi:10.1021/acs.joc.3c01181

Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides

J Org Chem. 2023 Nov 17;88(22):15969-15974. doi: 10.1021/acs.joc.3c01181. Epub 2023 Oct 30.

Authors

Shengkun Guo¹, Xiaoyu Shen¹, Xiaoyun Chen², Huaguang Yu³, Ying Han¹, Chaoguo Yan¹, Yaocheng Shi¹, Hong Hou¹, Shaoqun Zhu¹

Affiliations

¹ School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225009, P. R. China.
² School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212005, P. R. China.
³ Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, College of Optoelectronic Materials and Technology, Jianghan University, Wuhan 430056, P. R. China.

PMID: 37903348
DOI: 10.1021/acs.joc.3c01181

Abstract

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization with various nucleophiles.