A Robust and Broadly Applicable Cobalt-Catalyzed Cross-Coupling of Functionalized Bench-Stable Organozinc Pivalates with Unsaturated Halides

Jeffrey M Hammann; Ferdinand H Lutter; Diana Haas; Paul Knochel

doi:10.1002/anie.201610324

A Robust and Broadly Applicable Cobalt-Catalyzed Cross-Coupling of Functionalized Bench-Stable Organozinc Pivalates with Unsaturated Halides

Angew Chem Int Ed Engl. 2017 Jan 19;56(4):1082-1086. doi: 10.1002/anie.201610324. Epub 2016 Dec 16.

Authors

Jeffrey M Hammann¹, Ferdinand H Lutter¹, Diana Haas¹, Paul Knochel¹

Affiliation

¹ Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377, Munich, Germany.

PMID: 27981715
DOI: 10.1002/anie.201610324

Abstract

We report a robust and broadly applicable CoCl₂ -catalyzed cross-coupling between functionalized aryl and heteroaryl zinc pivalates and various electron-poor aryl and heteroaryl halides (X=Cl, Br, I). Couplings with (E)- or (Z)-bromo- or iodo-alkenes proceed with retention of configuration. Also, alkynyl bromides react with arylzinc pivalates providing arylated alkynes.

Keywords: N-heterocycles; cobalt; cross-coupling; zinc; zinc pivalate.

Publication types

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