Hydroboration. 97. Synthesis of New Exceptional Chloroborane-Lewis Base Adducts for Hydroboration. Dioxane-Monochloroborane as a Superior Reagent for the Selective Hydroboration of Terminal Alkenes

Josyula V. B. Kanth and Herbert C. Brown*

*H. C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, Email: hcbrownpurdue.edu

J. V. B. Kanth, H. C. Brown, J. Org. Chem, 2001, 66, 5359-5365.

DOI: 10.1021/jo015527o

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Abstract

Convenient methods for the preparation of stable and non-volatile mono- and dichloroborane adducts of dioxane from dioxane-BCl₃ and NaBH₄ in the presence of catalytic amounts of tri- or tetraglyme were developed. The dioxane-monochloroborane adduct hydroborates representative olefins cleanly and rapidly and lead to the corresponding alcohols in quantitative yields after oxidation.

preparation of borane reagents

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Key Words

Hydroboration, Alcohols, Hydrogen Peroxide

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ID: J42-Y2001-320