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45.13 Product Class 13: Biaryls

DOI: 10.1055/sos-SD-045-00510

Black, D. A.; Fagnou, K.Science of Synthesis, (201045547.

General Introduction

A biaryl core is found in a wide range of pharmaceutical agents, organic compounds, and natural products. Several methods exist for the preparation of biaryls, the oldest of which is copper-catalyzed Ullmann-type coupling. More recently, nickel- and palladium-catalyzed coupling reactions have evolved that enable the cross coupling of aryl halides and pseudohalides with organometallic nucleophiles. These innovations include the use of such named reactions as the Suzuki (via organoboronates), Stille (via organostannanes), Negishi (via organozincs), Hiyama (via organosilicons), and KumadaCorriu (via Grignard reagents) procedures. These reactions have been extensively explored since the 1980s and have revolutionized biaryl synthesis.[‌1‌‌5‌] Newer methods include direct arylation in which substitution of one of the preactivated arenes by a simple arene[‌6‌] minimizes preliminary work and the formation of toxic metallic byproducts.