18213-73-5Relevant academic research and scientific papers
Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids
Li, Xiao-Jian,Zhang, Jin-Ling,Geng, Yu,Jin, Zhong
, p. 5078 - 5084 (2013/06/27)
Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids was described. Selective activation of the phenol C-O bonds was achieved by converting them into the corresponding aryl 2,4-dimethoxy-1,3,5- triazine-6-yl ethers, in which aryl C-O bond could be selectively cleaved with inexpensive, air-stable NiCl2(dppf) as a catalyst. Coupling of these readily accessible heteroaryl ethers proved tolerant of extensive functional groups.
Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system
Silva, Marcio S.,Ferrarini, Renan S.,Sousa, Bruno A.,Toledo, Fabiano T.,Comasseto, Jo?o V.,Gariani, Rogério A.
supporting information; experimental part, p. 3556 - 3559 (2012/09/08)
We present a general protocol for the cross-coupling reaction of Grignard reagents and organic tellurides. Aryl Grignard reagents react stereospecifically with vinyl tellurides in the presence of a catalytic amount of manganese (II) chloride and copper (I) iodide to produce good yields of the corresponding cross-coupling products.
A mild robust generic protocol for the Suzuki reaction using an air stable catalyst
Moseley, Jonathan D.,Murray, Paul M.,Turp, Edward R.,Tyler, Simon N.G.,Burn, Ross T.
experimental part, p. 6010 - 6017 (2012/09/21)
A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility.
Organometallic alkylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine: A study
Samaritani, Simona,Signore, Giovanni,Malanga, Corrado,Menicagli, Rita
, p. 4475 - 4483 (2007/10/03)
The reactivity of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) has been investigated in Pd- or Ni-catalyzed cross-coupling processes with organostannanes, Grignard reagents, organoalanes and organozinc halides. All organometallic reagents considered form new C-C bonds on the heteroaromatic ring and afford the corresponding 2-alkyl-4,6-dimethoxy-1,3,5-triazines in moderate to very good yields. The collected data allows the choice of the alkylating agent as well as the experimental conditions depending on the residue to transfer.
Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging Suzuki coupling reactions
Colacot, Thomas J.,Shea, Helene A.
, p. 3731 - 3734 (2007/10/03)
(Chemical Equation Presented) The use of Cp2Fe(PR 2)2PdCl2 (R = i-Pr and t-Bu) in Suzuki coupling reactions were illustrated using a high throughput screening approach. The di-tbpfPdCl2 catalyst was shown to be the more active catalyst for unactivated and sterically challenging aryl chlorides. Comparison studies using the commercial catalysts dppfPdCl2, (Ph3P) 2PdCl2, (Cy3P)2PdCl2, DPEPhosPdCl2, dppbPdCl2, dppePdCl2, Pd(t-Bu3P)2, and [Pd-(μ-Br)(t-Bu3P)] 2 were also done for selected cases to demonstrate the superior activities of di-tbpfPdCl2 and di-isoppfPdCl2.
Iron catalyzed cross coupling reactions of aromatic compounds
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Page/Page column 16, (2010/02/03)
A process for the production of compounds Ar—R1 by means of a cross-coupling reaction of an organometallic reagent R1—M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.
Iron-catalyzed cross-coupling reactions
Fuerstner, Alois,Leitner, Andreas,Mendez, Maria,Krause, Helga
, p. 13856 - 13863 (2007/10/03)
Simple iron salts such as FeCln, Fe(acac)n (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl o
Combinatorial libraries with P-functionalized aminopyridines: Ligands for the preparation of efficient C(Aryl)-Cl activation catalysts
Schareina, Thomas,Kempe, Rhett
, p. 1521 - 1523 (2007/10/03)
The parallel synthesis of homogeneous catalysts is successful with ligands such as 1. They coordinate metals of Group 10 with the formation of a five-membered chelate ring (see scheme). The resulting metal complexes are efficient catalysts which can activ
