Sequential C-O decarboxylative vinylation/C-H arylation of cyclic oxalates via a nickel-catalyzed multicomponent radical cascade

Huan Li; Lei Guo; Xiaoliang Feng; Liping Huo; Shengqing Zhu; Lingling Chu

doi:10.1039/d0sc01471k

Sequential C-O decarboxylative vinylation/C-H arylation of cyclic oxalates via a nickel-catalyzed multicomponent radical cascade

Chem Sci. 2020 Apr 14;11(19):4904-4910. doi: 10.1039/d0sc01471k.

Authors

Huan Li¹, Lei Guo¹, Xiaoliang Feng¹, Liping Huo¹, Shengqing Zhu¹, Lingling Chu¹

Affiliation

¹ State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry, Chemical Engineering and Biotechnology, Center for Advanced Low-Dimension Materials, Donghua University Shanghai 201620 China Lingling.chu1@dhu.edu.cn.

Abstract

A selective, sequential C-O decarboxylative vinylation/C-H arylation of cyclic alcohol derivatives enabled by visible-light photoredox/nickel dual catalysis is described. This protocol utilizes a multicomponent radical cascade process, i.e. decarboxylative vinylation/1,5-HAT/aryl cross-coupling, to achieve efficient, site-selective dual-functionalization of saturated cyclic hydrocarbons in one single operation. This synergistic protocol provides straightforward access to sp³-enriched scaffolds and an alternative retrosynthetic disconnection to diversely functionalized saturated ring systems from the simple starting materials.