Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner

Xiangqian Yan; Fanzhi Yang; Guilong Cai; Qingwei Meng; Xiaofang Li

doi:10.1021/acs.orglett.7b03753

Nickel(0)-Catalyzed Inert C-O Bond Functionalization: Organo Rare-Earth Metal Complex as the Coupling Partner

Org Lett. 2018 Feb 2;20(3):624-627. doi: 10.1021/acs.orglett.7b03753. Epub 2018 Jan 10.

Authors

Xiangqian Yan¹, Fanzhi Yang², Guilong Cai¹, Qingwei Meng¹, Xiaofang Li¹

Affiliations

¹ School of Chemistry and Chemical Engineering, Key Laboratory of Cluster Science of Ministry of Education, Beijing Institute of Technology , 5 South Zhongguancun Street, Haidian District, Beijing 100081, China.
² Advanced Research Institute of Multidisciplinary Science, Beijing Institute of Technology , 5 South Zhongguancun Street, Haidian District, Beijing 100081, China.

PMID: 29320207
DOI: 10.1021/acs.orglett.7b03753

Abstract

An organo rare-earth metal complex has been employed as a highly efficient nucleophile in Ni(0)-catalyzed C-O bond functionalization. The optimized catalytic system which consists of Ni(cod)₂, PCy₃, and t-BuONa could smoothly convert 1 equiv of naphthyl ethers to alkylated naphthalene analogues with 0.4 equiv of Ln(CH₂SiMe₃)₃(THF)₂, delivering good to excellent yields. The reaction system could also activate the ArCH₂-O bond with mild base.

Publication types

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