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6.1.1.1.1.1 Variation 1: From Tetrahydroborate with Protic Acids

DOI: 10.1055/sos-SD-006-00003

Matteson, D. S.Science of Synthesis, (200568.

Protolysis of sodium borohydride with anhydrous hydrogen chloride to generate solutions of boranetetrahydrofuran (3) suitable for use in hydroboration was described by Brown and co-workers in 1960 (Scheme 3).[‌15‌] It is essential that the hydrogen chloride is not be used in greater than the stoichiometric amount, since borane is converted into chloroborane by hydrogen chloride. An alternative procedure involves the slow addition of a solution of sulfuric acid in tetrahydrofuran to a solution of lithium borohydride and the alkene to be hydroborated in tetrahydrofuran.

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