Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles

Lukasz Przypis; Krzysztof Zdzislaw Walczak

doi:10.1021/acs.joc.8b02821

Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles

J Org Chem. 2019 Feb 15;84(4):2287-2296. doi: 10.1021/acs.joc.8b02821. Epub 2019 Jan 30.

Authors

Lukasz Przypis¹, Krzysztof Zdzislaw Walczak¹

Affiliation

¹ Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology , Silesian University of Technology , Krzywoustego 4 , Gliwice 44-100 , Poland.

PMID: 30661359
DOI: 10.1021/acs.joc.8b02821

Abstract

A copper-catalyzed iodination of carbazoles has been developed. Barluenga's reagent IPy2BF4 is used to generate a soft electrophilic halonium species for the iodination of the carbazoles. This report represents the first concept of copper-catalyst-promoted electrophilic halogenation of carbazoles. We demonstrated numerous applications of this methodology synthesizing diverse carbazole derivatives, i.e., both electron-rich and electron-deficient systems.

Publication types

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