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The magnesium bromide diethyl etherate (MgBr2· OEt2)-methyl sulfide (Me2S) system is useful for the mild and chemo-selective deprotection of p-methoxybenzyl (PMB) ether. Lewis acid for catalysis of Diels-Alder reactions of homochiral 2-sulfinylmaleates with cyclopentadiene. Magnesium bromide diethyl etherate is used in the synthesis of silicon-containing azole derivatives.
Satomi Hirasawa,; Hajime Nagano,; Yoko Kameda. Conjugate reduction of aryl acrylates with tributyltin hydride in the presence of magnesium bromide diethyl etherate. Tetrahedron Letters. year of publication , 45(10), 2207-2209.
Toshihiko Onoda,; Ryuichi Shirai,; Shigeo Iwasaki. A mild and selective deprotection of p-methoxybenzyl (PMB) ether by magnesium bromide diethyl etherate-methyl sulfide. Tetrahedron Letters. 1997, 38 (8), 1443-1446.
Lewis acid which can influence the regio- and stereochemical outcome of reactions because of its chelating character. Mediates the rearrangement of epoxides to aldehydes and ketones: J. Am. Chem. Soc., 77, 5083 (1955); Tetrahedron Lett., 33, 4457 (1992); or ring-opening to bromohydrins: J. Org. Chem., 61, 3557 (1996); 68, 3660 (2003); Tetrahedron Lett., 45, 5969 (2004). Promotes anti-selectivity in aldol reactions: J. Org. Chem., 56, 5978 (1991). Activates amides to selective N-acylation: Tetrahedron Lett., 43, 647 (2002).
In combination with Me2S, promotes chemoselective deprotection of p-methoxybenzyl ethers, in the presence of benzyl or TBDMS ethers, benzoate esters or acetonides: Tetrahedron Lett., 38, 1443 (1997). In the presence of triethylamine, promotes the room-temperature Cannizzaro reaction of aryl and heteroaryl aldehydes to the corresponding alcohol and carboxylic acid: Org. Lett., 7, 5893 (2005).
For a brief feature on uses of this reagent, see: Synlett, 912 (2004).
Hazard Statements: H228-H500
Flammable solid. May form combustible dust concentrations in air
Precautionary Statements: P210-P240-P241-P280-P370+P378q
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use CO2, dry chemical, or foam