154197-00-9Relevant articles and documents
Suzuki–Miyaura Cross-Coupling in Aqueous Medium Using Recyclable Palladium/Amide-Silica Catalyst
Mondal, Manoj,Dewan, Anindita,Begum, Tahshina,Gogoi, Pradip K.,Thakur, Ashim Jyoti,Bora, Utpal
, p. 1718 - 1728 (2016)
Abstract: Silica-immobilized benzamide palladium complex was prepared and characterized. The complex exhibits excellent catalytic activity and stability for Suzuki–Miyaura cross-coupling reaction under mild aqueous reaction condition. Various aryl bromide
Rapid Suzuki-Miyaura cross-coupling reaction catalyzed by zirconium carboxyphosphonate supported mixed valent Pd(0)/Pd(II) catalyst
Bhattacharyya, Bagmita,Biswas, Jyoti Prasad,Mishra, Shashank,Gogoi, Nayanmoni
, (2019)
Mixed valent Pd(0)/Pd(II) nano-sized aggregates supported onto a chemically robust layered zirconium carboxyphosphonate framework is prepared and its catalytic activity in Suzuki-Miyaura cross coupling reaction is explored. The exceptionally high catalytic efficacy of the heterogeneous catalyst in Suzuki-Miyaura cross coupling reaction is signified by remarkably short reaction time 2?minutes and high turnover frequency of 1.3 x 104?hr?1. The catalyst can be recycled several times without significant loss of catalytic efficacy, while spectroscopic, structural and microscopic investigations suggest the integrity of the catalyst even after fifth catalytic cycle. The unique ability of the zirconium carboxyphosphonate framework to interact strongly with palladium in dual Pd(0)/Pd(II) oxidation states has been attributed to this remarkable augmentation of catalytic efficacy.
A Highly Efficient Monophosphine Ligand for Parts per Million Levels Pd-Catalyzed Suzuki–Miyaura Coupling of (Hetero)Aryl Chlorides
Choy, Pui Ying,Yuen, On Ying,Leung, Man Pan,Chow, Wing Kin,Kwong, Fuk Yee
, p. 2846 - 2853 (2020/04/09)
A new indolylphosphine WK-phos has been synthesized for Pd-catalyzed Suzuki–Miyaura coupling of (hetero)aryl chlorides with (alkyl)arylboronic acids. Comprising this newly developed ligand with palladium(II) acetate, the resulting catalyst system was found to be highly effective in facilitating the reaction even when the catalyst loading reaches parts per million levels (e.g. 10 ppm). These examples represent one of the lowest catalyst loadings reported to date of employing monophosphine (e.g. Ar-PCy2) for Suzuki–Miyaura reactions. The ligand geometry has also been well-characterized by single-crystal X-ray crystallography.
LiCl-Accelerated multimetallic cross-coupling of aryl chlorides with aryl triflates
Huang, Liangbin,Ackerman, Laura K. G.,Kang, Kai,Parsons, Astrid M.,Weix, Daniel J.
supporting information, p. 10978 - 10983 (2019/08/07)
While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.
A Molecular/Heterogeneous Nickel Catalyst for Suzuki-Miyaura Coupling
Key, Ryan J.,Tengco, John Meynard M.,Smith, Mark D.,Vannucci, Aaron K.
, p. 2007 - 2014 (2019/05/16)
A molecular/heterogeneous catalyst motif based on an earth abundant nickel catalyst and SiO2 support has been designed and synthesized. Characterization and catalytic testing indicate that the molecular nickel catalyst [(2,2′:6′,2′′-terpyridine-4′-benzoic acid)Ni(II)]Cl2 attached to a high surface area SiO2 support is the active cross-coupling catalyst and increased product yields are a result of increased molecular stability of the catalyst while attached to the SiO2 support. This molecular/heterogeneous motif is easily separated from reaction mixtures and can be recycled for multiple catalytic reactions. The catalyst is active for Suzuki-Miyaura catalysis at catalyst loadings as low as 0.1 mol %, and turnover numbers nearing 2000 have been achieved.
