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...

Iodine-catalyzed condensation of 2-amino-3,5-dibromobenzamide with cyclohexane-1,3-dione derivatives in refluxing toluene afforded the corresponding bisquinazolinones. Suzuki-Miyaura cross-coupling of the latter with arylboronic acids afforded tetraarylbisquinazolinones. The electronic absorption and emission properties of these tetraarylbisquinazolinones were measured in dimethylsulfoxide (DMS...

We report the development of a method for direct Chan–Lam coupling arylboronic acid N -methyliminodiacetic esters (ArBMIDA). The process accommodates amine and alcohol nucleophiles to deliver wide range C–N C–O cross-coupled products in 34–99% yield (34 examples). This serves expand scope organoboron component that can be used directly this oxidative reaction provides opportunities streamlining...

[Ru(p-cymene)Cl2]2-catalyzed 1,4-addition reactions between arylboronic acids and butyl acrylate and acrylamide in the presence of phenols were investigated, good to excellent yields were obtained. The addition of phenols remarkably promoted the protonolysis and inhibited the β-H elimination of the 1,4-addition intermediates, and also efficiently suppressed the protonolysis of arylboronic acids.

We report a synthetic platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful intermediates but commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation arylboronic acids provides access these compounds that, in turn, allow C–C, C–O, and C–N bonds from Pd- Cu-mediated cross-c...

Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomeri...

The first Suzuki cross-coupling reaction of aryltrimethylammonium triflates based on the use of an IMes.Ni(0) catalyst system is described. A wide range of electron-withdrawing and electron-donating substituents are tolerated on both the aryltrimethylammonium triflate and the boronic acid components of this reaction. In addition to arylboronic acids, the scope of the reaction is extended to enc...

Palladium catalyzed Suzuki-Miyaura cross-coupling of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with arylboronic and arylvinylboronic acid derivatives in the presence of potassium carbonate in aqueous dioxane afforded the corresponding 4,6,8-triarylquinoline-3-carbaldehydes, exclusively. These products were transformed into 4,6,8-triaryl-3-(4-fluorophenyl)amino)-N-(quinolin-3-yl)methylenes an...

The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2' mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum ...