Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction

Jiyao Han; Xiaowei Sun; Xiao Wang; Qiong Wang; Shenghuai Hou; Xin Song; Yingqin Wei; Rongyu Wang; Wenhua Ji

doi:10.1021/acs.orglett.0c00061

Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction

Org Lett. 2020 Feb 21;22(4):1480-1484. doi: 10.1021/acs.orglett.0c00061. Epub 2020 Feb 3.

Authors

Jiyao Han¹, Xiaowei Sun², Xiao Wang², Qiong Wang³, Shenghuai Hou², Xin Song², Yingqin Wei¹, Rongyu Wang², Wenhua Ji²

Affiliations

¹ School of Chemistry and Pharmaceutical Engineering , Qilu University of Technology (Shandong Academy of Sciences) , Jinan 250353 , China.
² School of Pharmaceutical Sciences, Shandong Analysis and Test Center , Qilu University of Technology (Shandong Academy of Sciences) , Jinan 250014 , China.
³ College of Chemistry, Chemical Engineering and Materials Science , Shandong Normal University , Jinan 250014 , China.

PMID: 32009410
DOI: 10.1021/acs.orglett.0c00061

Abstract

A simple imine-based covalent organic framework (COF) as heterogeneous ligand for Pd^II-promoted Heck reaction is reported. Good regioselectivity for a wide range of electronically unbiased olefins is obtained (linear/branched >100:1 in most cases). Related tests and density functional theory calculations are used to explore the reason underlying the high selectivity. This research opens a route for COF as an intriguing platform to control regioselectivity catalysis.