A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid

Gary A Molander; Sarah L J Trice; Brittany Tschaen

doi:10.1016/j.tet.2015.04.026

A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid

Tetrahedron. 2015 Sep 2;71(35):5758-5764. doi: 10.1016/j.tet.2015.04.026.

Authors

Gary A Molander¹, Sarah L J Trice¹, Brittany Tschaen¹

Affiliation

¹ Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323.

Abstract

A modified Pd-catalyzed method of forming aryl- and heteroarylboron species and a two-step, one-pot borylation/Suzuki-Miyaura cross coupling using the atom economical tetrahydroxydiboron (bis-boronic acid, BBA) is reported. By using ethylene glycol as an additive, the new method results in increased yields, lower BBA loading, faster reaction times, and a broader reaction scope, including previously problematic substrates such as heterocycles.

Keywords: Borylation; Cross-Coupling; Tetrahydroxydiboron; bis-Boronic Acid.

Abstract

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