Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene pi-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine.
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Scheideman et al. (2003) studied this question.
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