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Issue 6, 2001
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A new facile approach to highly selective hydroboration of alkenes with sodium malonyloxyborohydride

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Abstract

The preparation and properties of sodium malonyloxyborohydride (SMB) are described. As a white solid, SMB is very sensitive to moisture in air. It is also highly sensitive to the structure of alkenes. Thus SMB, prepared in situ from the reaction of malonic acid with equimolar NaBH4 in dry THF, hydroborates alkenes showing that terminal aliphatic alkenes undergo facile hydroboration with 98% of the boron moiety placed on the terminal position and 2% at the 2 position. On the other hand, trisubstituted alkenes and cyclohexene show poor reactivity in the hydroboration as compared with terminal alkenes. These characteristics indicate that SMB is a highly regioselective monofunctional hydroborating reagent for terminal alkenes.

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Publication details

The article was received on 04 Jan 2001, accepted on 21 Mar 2001 and first published on 14 May 2001


Article type: Paper
DOI: 10.1039/B100228G
Citation: New J. Chem., 2001,25, 869-871

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    A new facile approach to highly selective hydroboration of alkenes with sodium malonyloxyborohydride

    S. Huang, W. Peng, Z. Shan and D. Zhao, New J. Chem., 2001, 25, 869
    DOI: 10.1039/B100228G

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