90226-51-0Relevant academic research and scientific papers
Amine-directed hydroboration: Scope and limitations
Scheideman, Matthew,Wang, Guoqiang,Vedejs, Edwin
supporting information; experimental part, p. 8669 - 8676 (2009/02/03)
Iodine activation induces intramolecular hydroboration of homoallylic and bis-homoallylic amine boranes with good to excellent control of regiochemistry compared to control experiments using excess THF?BH3. Deuterium labeling and other evidence confirm that the iodine-induced hydroboration reaction of homoallylic amine boranes occurs via an intramolecular mechanism equivalent to the classical 4-center process and without competing retro-hydroboration. Longer carbon chain tethers result in lower regioselectivity, whereas the shorter tether in allylic amines results in a switch to dominant intermolecular hydroboration. Regioselectivity in THF?BH3 control experiments is higher for the allylic amine boranes compared to the iodine activation experiments, whereas the reverse is true for homoallylic amine borane activation.
A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes
Scheideman, Matthew,Shapland, Peter,Vedejs, Edwin
, p. 10502 - 10503 (2007/10/03)
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 π-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine. Copyright
