Highly efficient amine‐based catalytic system for room temperature Suzuki–Miyaura reactions of aryl halides with arylboronic acids

Abstract

An in situ-generated catalytic system based on PdCl 2 and primary amine-based ligand exhibited excellent activity (up to 98% isolated yield) in the Suzuki-Miyaura cross-coupling reactions of aryl bromides with arylboronic acids in water, at room temperature, without any additive. The efficiencies of the ligands follow the order: (C 6 H 5 ) 3 CNH 2 > C 6 H 5 CH 2 NH 2 > C 6 H 5 NH 2 > C 6 H 11 NH 2 , which is in accordance with the palladacycle forming capacity of the respective ligands. Moderate-to-good yields (up to 78% isolated yield) of the coupling products were also obtained with less reactive aryl chlorides as substrates at room temperature in isopropanol using an alternative protocol based on Pd(OAc) 2 and (C 6 H 5 ) 3 CNH 2 .

Extraction of Base from Eichhornia crassipes and Its Implication in Palladium‐Catalyzed Suzuki Cross‐Coupling Reaction

“…Usually, catalytic systems for these transformations are composed of Pd(0) or Pd(II) derivatives. Recently, different ligands such as N‐heterocyclic carbenes, amines, oximes,, amides, and their co‐ordination with palladium have attracted considerable attention as catalyst for Suzuki‐Miyaura Cross‐Coupling reaction. However, in most of the cases, main disadvantages associated are the availability, stability and cost of the Pd complexes and associated ligands and their moisture sensitivity.…”

Embossing of organic thin films using a surfactant assisted lift-off technique

“…Trinitrotoluene (TNT) and 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX) were obtained from Austin Explosive, Austin, TX, with purity of 99%. (E)-4-(4-nitrostyryl)-N,N-diphenylaniline (NSDPA), biphenyl-4-carboxylic acid (BCA), 2,4,7-trinitrofluorenone (TNF), and 2,7-dibromo-4-nitrofluorenone (DBNF) were synthesized from literature protocols, with purity of 99% (the experimental details and characterization data for these four compounds are given in ESI) [37][38][39][40]. Nitrocellulose (NC; 4-8% in ethanol/diethyl ether), carbazole (>95%), hexadecyl-trimethylammonium bromide (CTAB; 99%), tetra-n-butylammonium bromide (TBAB; 99%), didecyldimethylammonium bromide (99%), naphthalene (99%), poly(methyl methacrylate) (PMMA, average Mn = 10,400), polystyrene (PS, average Mn = 4020), and poly(dimethylsiloxane) (PDMS, average Mn = 4020) used for this study were purchased from SigmaAldrich Inc. Al (99.999%), Au (99.99%), Cu (99.99%), Cr (99.998%), and Ni (99.995%) are purchased from Kurt J. Lesker Company.…”

Ligandless heterogeneous palladium: an efficient and recyclable catalyst for Suzuki‐type cross‐coupling reaction

“…Moreover, the catalytic system could be recycled repeatedly without any loss in activity and efficiency. Since 2010, our laboratory has emphasized the improvement of reactions involving easily accessible organoborons, and a series of transformations have been reported . According to accessible literatures, Pd/C has been demonstrated as an effective, commercially available heterogeneous catalyst for Suzuki–Miyaura cross‐coupling reactions, but have never been studied in Suzuki‐type cross‐coupling reactions of acid halides and arylboronic acids.…”