Synthesis, Regioselective Bromination, and Functionalization of Coronene Tetracarboxydiimide

Taifeng Liu; Yongchao Ge; Baolai Sun; Brandon Fowler; Hexing Li; Colin Nuckolls; Shengxiong Xiao

doi:10.1021/acs.joc.8b03129

Synthesis, Regioselective Bromination, and Functionalization of Coronene Tetracarboxydiimide

J Org Chem. 2019 Mar 1;84(5):2713-2720. doi: 10.1021/acs.joc.8b03129. Epub 2019 Feb 20.

Authors

Taifeng Liu^{1

2}, Yongchao Ge¹, Baolai Sun¹, Brandon Fowler², Hexing Li¹, Colin Nuckolls^{1

2}, Shengxiong Xiao¹

Affiliations

¹ The Education Ministry Key Lab and International Joint Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Optoelectronic Nano Materials and Devices Institute , Shanghai Normal University , Shanghai 200234 , China.
² Department of Chemistry , Columbia University , New York , New York 10027 , United State.

PMID: 30734564
DOI: 10.1021/acs.joc.8b03129

Abstract

A new method for the effective synthesis of coronene tetracarboxydiimide (CDI) was developed by utilizing inexpensive and nontoxic potassium vinyltrifluoroborate. Controllable brominations of CDI were accomplished to yield CDI mono-, di-, tri-, and tetra-bromides, which could be used as synthon and functionalized by aromatic nucleophilic substitution and the Sonogashira coupling reaction.

Publication types

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