72358-72-6Relevant academic research and scientific papers
Palladium-catalyzed intra-and intermolecular C-H arylation using mesylates: Synthetic scope and mechanistic studies
Ferguson, Devin M.,Rudolph, Stacey R.,Kalyani, Dipannita
, p. 2395 - 2401 (2014/07/21)
This paper describes the development of Pd-catalyzed inter-and intramolecular direct arylation using mesylates. Furthermore, a sequential mesylation/arylation protocol using phenols as substrates is described. These transformations are general with respect to the electronics of the C-H substrates and allow for the synthesis of diverse heterocyclic motifs in good yields. Both arenes and heteroarenes efficiently participate in these reactions. Preliminary mechanistic studies are presented for both inter-and intramolecular arylations.
Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn
Wilson, Daniela A.,Wilson, Christopher J.,Moldoveanu, Costel,Resmerita, Ana-Maria,Corcoran, Patrick,Hoang, Lisa M.,Rosen, Brad M.,Percec, Virgil
supporting information; experimental part, p. 1800 - 1801 (2010/04/24)
(Chemical Presented) The mixed-ligand system NiCl2(dppp)/dppf is shown to be an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electrondeficient aryl mesylates and tosylates. The ad
A novel synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers using a mixture of phosphorus pentoxide in methanesulfonic acid
Kaboudin, Babak,Abedi, Yaghoub
experimental part, p. 2025 - 2028 (2009/12/26)
A simple, efficient, and new method has been developed for the synthesis of aryl mesylates via one-pot demethylation-mesylation of aryl methyl ethers. Treatment of a variety of aryl methyl ethers with a mixture of phosphorus pentoxide in methanesulfonic a
Mild cleavage of aryl mesylates: Methanesulfonate as potent protecting group for phenols
Ritter, Tobias,Stanek, Kyrill,Larrosa, Igor,Carreira, Erick M.
, p. 1513 - 1514 (2007/10/03)
A mild protocol for the chemoselective deprotection of aryl methanesulfonates is described. The transformation can be conducted on highly functionalized substrates and renders the methanesulfonate a useful, previously underutilized protecting group for phenols.
Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates
Kobayashi, Yuichi,William, Anthony D.,Mizojiri, Ryo
, p. 91 - 97 (2007/10/03)
Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-with-drawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)2 to furnish the coupling products in good yields.
Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates
Percec, Virgil,Bae, Jin-Young,Zhao, Mingyang,Hill, Dale H.
, p. 176 - 185 (2007/10/02)
Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ.This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls.The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated.In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.
