Radical modulated regioselective difunctionalization of vinyl enynes: tunable access to naphthalen-1(2 H)-ones and allenic alcohols

Xiao-Yu Xie; Yun-Fang Xu; Yang Li; Xiao-Dong Wang; Jie Zhu; Lei Wu

doi:10.1039/d1cc06994b

Radical modulated regioselective difunctionalization of vinyl enynes: tunable access to naphthalen-1(2 H)-ones and allenic alcohols

Chem Commun (Camb). 2022 Mar 1;58(18):3031-3034. doi: 10.1039/d1cc06994b.

Authors

Xiao-Yu Xie¹, Yun-Fang Xu¹, Yang Li¹, Xiao-Dong Wang¹, Jie Zhu¹, Lei Wu^{1

2}

Affiliations

¹ Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. China. zhujie@njau.edu.cn.
² College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, P. R. China.

PMID: 35156673
DOI: 10.1039/d1cc06994b

Abstract

A novel and efficient radical-modulated difunctionalization of vinyl enynes has been disclosed using TEMPO as a radical regulator. Facile access to structurally diverse 3-bromo-naphthalen-1(2H)-ones and 4-bromo-allenic alcohols was realized via 1,2-addition/1,2-migration or 1,4-addition, respectively. This protocol represents the first example of radical-modulated metal-free difunctionalization of 1,3-enynes with high regioselectivity.