Borane-methyl sulfide complex

Description

Borane dimethylsulfide (BMS) is a complex of borane with dimethylsulfide. The other common complex of borane is borane-THF. BMS is more stable than borane-THF and is therefore available in higher concentrations. BMS has the drawback of being smelly due to its dimethylsulfide content.

The Uses of Borane-methyl sulfide complex

Borane-dimethyl sulfide complex is used for hydroborations and reductions. Used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones. CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols. Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.

The Uses of Borane-methyl sulfide complex

To a solution of the SM (1.0 g, 6.4 mmol) in THF (18 mL) at 0 C was added BH3-SMe2 (6.4 mL, 12.8 mmol). The reaction mixture was stirred at 0 C for 2 h, then RT for 3 h. The mixture was cooled to 0 C and quenched with sat aq K2CO3 (5 mL). The layers were separated and the aq layer was extracted with EtOAc (2 x 15 mL) and diethyl ether (2 x 15 mL). The combined org layers were dried (Na2SO4) and concentrated to provide the product as a colorless oil. [1.0 g, 100 %]

What are the applications of Application

Borane dimethyl sulfide complex is a convenient and stable source of borane