Hydroboration. XXXIX. 1, 3, 2-Benzodioxaborole (catecholborane) as a new hydroboration reagent for alkenes and alkynes. General synthesis of alkane-and …

HC Brown, SK Gupta

Index: Brown,H.C.; Gupta,S.K. Journal of the American Chemical Society, 1975 , vol. 97, p. 5249 - 5255

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Citation Number: 202

Abstract

Abstract: Catecholborane (1, 3, 2-benzodioxaborole), readily available from the reaction of catechol with borane in THF, reacts rapidly with alkenes and alkynes at 100 and 70'. respectively, to give the corresponding alkyl-and alkenylcatecholboranes in high yield. These hydroborations proceed stereospecifically in a cis manner. Greater regioselectivity is realized in comparison with such hydroborations with diborane itself. The alkyl-and ...