Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

Si-Cong Chen; Qi Zhu; Yuhui Cao; Chen Li; Yinliang Guo; Lingran Kong; Jinteng Che; Zhixian Guo; Han Chen; Nan Zhang; Xianhe Fang; Jia-Tian Lu; Tuoping Luo

doi:10.1021/jacs.1c05092

Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

J Am Chem Soc. 2021 Sep 8;143(35):14046-14052. doi: 10.1021/jacs.1c05092. Epub 2021 Aug 26.

Authors

Si-Cong Chen¹, Qi Zhu¹, Yuhui Cao¹, Chen Li¹, Yinliang Guo¹, Lingran Kong¹, Jinteng Che², Zhixian Guo¹, Han Chen¹, Nan Zhang², Xianhe Fang², Jia-Tian Lu³, Tuoping Luo^{1

2

3}

Affiliations

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
² Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871, China.
³ Institute of Molecular Physiology, Shenzhen Bay Laboratory, Shenzhen, Guangdong 518055, China.

PMID: 34437800
DOI: 10.1021/jacs.1c05092

Abstract

A new and general method to functionalize the C(sp³)-C(sp²) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp³)-C(sp²) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.

Publication types

Research Support, Non-U.S. Gov't