Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding
Lei, Xiangyang,Jalla, Anusha,Abou Shama, Mhd A.,Stafford, Jamie M.,Cao, Billy
supporting information
p. 2578 - 2585
(2015/09/01)
Palladium-catalyzed carbonylation of aryl tosylates and mesylates
A general protocol for the palladium-catalyzed carbonylation of aryl tosylates and mesylates to form esters has been developed using a catalyst system derived from Pd(OAc)2 and the bulky, bidentate dcpp ligand. The system operates under mild conditions: atmospheric CO pressure and temperatures of 80-110 °C. A broad substrate scope has been demonstrated allowing carbonylation of electron-rich, electron-poor, and heterocyclic tosylates and mesylates, and the reaction shows wide functional group tolerance. Copyright
Munday, Rachel H.,Martinelli, Joseph R.,Buchwald, Stephen L.
p. 2754 - 2755
(2008/09/19)
A simple preparation of aryl methanesulfonates by thermal decomposition of dry arenediazonium O-benzenedisulfonimides in methanesulfonic acid
Aryl methansulfonates 3 (18 examples) were easily prepared by thermal decomposition of dry arenediazonium o-benzenedisulfonimides 1 in methanesulfonic acid (2). The reactions were carried out at temperatures between 60 and 120°C for times between 0.5 and 8 h. The aryl methanesulfonates were obtained in reproducible yield of 70-90%, with few exceptions. In all cases the o-benzenedisulfonimide (4) could be recovered in good yields which can then be reused to prepare the salts 1. When thermal decomposition of salts 1 was carried out in trifluoromethanesulfonic acid (5) at 90-120°C for 1-2 h, aryl trifluoromethanesulfonates 6 were obtained in 73-78% yield (3 examples).
Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita,Perracino, Paolo
p. 90 - 93
(2007/10/03)
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