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Methanesulfinic acid sodium salt is used in the preparation of alkyl methyl sulfone and methyl bis(4-tolyl)sulfoniumtrifluoromethanesulfonate. It is also employed in the synthesis of two sulfonyl type reversible addition-fragmentation transfer (RAFT) agents such as benzyl methylsulfonyldithioformate and benzyl phenylsulfonyldithioformate.
Nucleophilic reagent for preparation of alkyl methyl sulfones: J. Am. Chem. Soc., 75, 5582 (1953). Aryl methyl sulfones are formed by SNAr displacement of activated p-fluoro or p-chloro substituents from aryl aldehydes, ketones, nitriles or nitro compounds in DMSO: J. Org. Chem., 54, 4691 (1989). In the presence of CuI in DMF, displacement of non-activated iodoarenes occurs: Tetrahedron Lett., 36, 6239 (1995); see also: J. Org. Chem., 70, 2696 (2005). Under similar conditions, selective displacement of an aryl bromo substituent in the presence of an aryl fluoro can be effected.: J. Org. Chem., 70, 268 (2005). Arylboronic acids undergo displacement with the reagent under mild conditions in the presence of copper(II) acetate in DMF or DMSO; selective displacement of the boronate group from 3-bromobenzeneboronic acid is possible: Tetrahedron Lett., 45, 3233 (2004).
Xu, Y.; Tang, X.; Hu, W.; Wu, W.; Jiang, H. Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids. Green Chem. 2014, 16 (8), 3720-3723.
Pike, K. G.; Morris, J.; Ruston, L.; Pass, S. L.; Greenwood, R.; Williams, E. J.; Demeritt, J.; Culshaw, J. D.; Gill, K.; Pass, M.; Finlay, M. R. V.; Good, C. J.; Roberts, C. A.; Currie, G. S.; Blades, K.; Eden, J. M.; Pearson, S. E. Discovery of AZD3147: A Potent, Selective Dual Inhibitor of mTORC1 and mTORC2. J. Med. Chem. 2015, 58 (5), 2326-2349.
Gefahrenhinweise (EU): H302
Harmful if swallowed.
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