10355-12-1Relevant articles and documents
Thieme journal awardees - Where are they now? on cobalt-catalyzed biaryl coupling reactions
Mayer, Matthias,Czaplik, Waldemar Maximilian,Jacobi Von Wangelin, Axel
, p. 2919 - 2923 (2009)
An operationally simple biaryl coupling reaction has been developed. The underlying domino process involves in situ Grignard formation from aryl bromides and subsequent homocoupling with catalytic CoCl2 and 1 bar synthetic air as terminal oxidant. Georg Thieme Verlag Stuttgart.
Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols
Denmark, Scott E.,Ober, Michael H.
, p. 1703 - 1714 (2004)
Cesium carbonate and cesium hydroxide monohydrate are effective activators for the palladium-catalyzed cross-coupling of aryl(dimethyl)silanols with substituted aryl halides. Extensive optimization studies led to the identification of key variables (solvent, catalyst, additive, and hydration level) that influence the rate and selectivity of the process. Manipulation of these factors provides an effective coupling method of wide scope and generality. Electron-rich aryl(dimethyl)silanols undergo cross-coupling with aryl iodides and aryl bromides in high yields and high selectivity for the desired cross-coupling products. Alternatively, high yields of cross-coupling products could be obtained with electron-poor or ortho-substituted aryl(dimethyl)silanols when activated with cesium hydroxide monohydrate.
Nickel(II)/N-Heterocyclic Carbene Catalyzed Desulfinylative Arylation by C?S Cleavage of Aryl Sulfoxides with Phenylboronic Acids
Yi, Xiaowen,Chen, Kai,Guo, Junjun,Chen, Wei,Chen, Wanzhi
supporting information, p. 4373 - 4377 (2020/07/27)
Suzuki-Miyaura coupling of haloarenes is the most widely used protocol for the synthesis of biphenyls. Organosulfur compounds are promising electrophiles since they are abundant in nature and versatile in organic synthesis. We report here the desulfinylative Suzuki-Miyaura coupling of aryl sulfoxides with phenylboronic acids using bench-stable nickel/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily prepared from common commercial chemicals. The method is applicable to both symmetric and unsymmetric aryl sulfoxides, and a range of biphenyls bearing various functional groups were obtained in up to 94% yield. (Figure presented.).
Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids
Laberge, Nicole A.,Love, Jennifer A.
supporting information, p. 5546 - 5553 (2015/09/01)
A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.
Platinum-catalyzed C-H arylation of simple arenes
Wagner, Anna M.,Hickman, Amanda J.,Sanford, Melanie S.
, p. 15710 - 15713 (2013/11/06)
This report describes the Na2PtCl4 catalyzed C-H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl 4 as the catalyst. Preliminary mechanistic studies provide evidence for a PtII/PtIV catalytic cycle involving rate-limiting C-C bond-forming reductive elimination.