Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids

Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc00367f Click here for additional data file.

Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides.

A protocol for the Suzuki-Miyaura coupling of heteroaryl boronic acids and vinyl chlorides that minimizes protodeboronation is described. A combination of catalytic amounts of Pd(OAc)(2) and SPhos in conjunction with CsF in isopropanol effectively affords a variety of coupled products. Surprisingly, a dramatic temperature dependence in product selectivity was observed.

Carbonylative Suzuki Couplings of Aryl Bromides with Boronic Acid Derivatives under Base-Free Conditions

The carbonylative Suzuki-Miyaura reaction between aryl bromides and arylboronic acid equivalents is herein reported, using base-free conditions and a limited excess of carbon monoxide generated ex situ from stable CO-precursors. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of the triglyceride and chole...

Carbonylative coupling of allylic acetates with aryl boronic acids.

The first allylic carbonylation reaction of allylic acetates with aryl boronic acids under carbon monoxide has been developed. Using Pd-PCy3 as a catalyst, a wide spectrum of allylic acetates was carbonylated in the presence of various aryl boronic acids, affording α,β-unsaturated aryl ketones in good to excellent yields. Preliminary studies indicate that carbon monoxide always inserts at the l...

Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Here...