Anti-Markovnikov Hydroamination of Homoallylic Amines

Hydroamination, or the addition of an amine across an unsaturated C–C bond, is an attractive disconnection for C–N bond formation. Not only is this reaction completely atom-economical, but this transformation readily couples two easily accessed functional groups. Hydroamination can form either the Markovnikov product or the anti-Markovnikov product, where the C–N bond is formed at either the internal or terminal position of the olefin, respectively. Metal catalysts are often used for promoting hydroamination reactions, which are generally hampered by high activation energy and unfavorable entropy. While the Markovnikov selective addition of an N–H bond across an alkene is relatively well known, direct anti-Markovnikov hydroamination has remained a significant challenge, in particular, as it requires the nucleophilic amine to attack the less electrophilic terminal carbon and results in the formation of the more sterically encumbered internal [M]–C bond. The group of Professor Kami Hull at the University of Illinois at Urbana–Champaign (USA) is interested in studying alternative strategies for controlling the selectivity of olefin functionalization reactions.

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