482377-56-0Relevant academic research and scientific papers
Efficient recycling in Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids using polymer-supported aryldicyclohexylphosphine
Glegola, Katarzyna,Framery, Eric,Pietrusiewicz, K. Michal,Sinou, Denis
, p. 1728 - 1733 (2006)
The synthesis of polymer-supported aryldicyclohexylphosphines has been developed. The catalytic performance of these ligands has been demonstrated in the Suzuki-Miyaura cross-coupling reaction of aryl chlorides with arylboronic acids. Concerning the recycling of the catalyst, the ligand based on copolymer polyethylene glycol/polystyrene showed a very high activity which was maintained during 6 runs.
'Click' Dendritic phosphines: Design, synthesis, application in Suzuki coupling, and recycling by nanofiltration
Janssen, Michele,Mueller, Christian,Vogt, Dieter
supporting information; experimental part, p. 313 - 318 (2009/10/20)
A new synthetic route towards stable molecular-weight enlarged monodentate phosphine ligands via 'click' chemistry was developed. These ligands were applied in the Pd-catalyzed Suzuki-Miyaura coupling of aryl halides and phenyl boronic acid. The supported systems show very similar activities compared to the unsupported analogues. Moreover, recycling experiments by means of nanofiltration using ceramic nanofiltration membranes demonstrate that these systems can be recovered and reused efficiently.
Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands
Nishimura, Masato,Ueda, Masato,Miyaura, Norio
, p. 5779 - 5787 (2007/10/03)
Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2′-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2′-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)2 and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)3 (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)2 (0.001mol%) and 10 (0.002mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water.
