791068-92-3Relevant articles and documents
Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant
Quibell, Jacob M.,Duan, Guojian,Perry, Gregory J.P.,Larrosa, Igor
supporting information, p. 6445 - 6448 (2019/06/07)
A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.
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.
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.
