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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 6
June 20, 1988 

Facile Reduction of Carboxylic Acid Salts to Aldehydes by Boron Hydrides Thexylbromoborane-Dimethyl Sulfide and 9-Borabicyclo [3.3.1]nonane
Jin Soon Cha*, Kwang Woo Lee, Mal Sook Yoon, Jae Cheol Lee, Jin Euog Kim
New methods of the reduction of carboxylic acid salts to aldehydes with 2 equiv of thexylbromoborane-dimethyl sulfide (ThxBHBr· SMe2) or 9-borabicyclo[3.3.1]nonane (9-BBN) are described. Both these reagents provide the corresponding aldehydes from various as sodium and lithium salts of carboxylic acids in high yields both at room temperature. Such facile reductions are explained as the simple substitution for the bromo group of ThxBHBr by a carboxylate to form thexyl(acyloxty)borane followed by reduction with excess reagent and the formation of an ate complex followed by reduction with excess 9-BBN.
384 - 388
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