Hydroamination, the direct addition of a C-N bond across an unsaturated C-C bond is an attractive synthetic method to access amine products which are commonly found in pharmaceutically relevant compounds.<sup>1</sup> Although great progress has been made in the field of early transition metal-catalyzed hydroamination, controlling regio- and chemoselectivity still remains a critical challenge. In a previous study in our group, we demonstrated the first example of Ti-catalyzed directed alkyne hydroamination which achieves complete regioselectivity with the aid of dative directing groups.<sup>2</sup> Intrigued by this observation, we conducted kinetic study on Ti-catalyzed alkyne hydroamination mediated by heteroatom donors to explore the origin of this regioselectivity. Reactions of 1-methoxyoct-3-yne and 1-(1-heyxn-1-yl)-2-methoxybenzene with aniline were investigated. We herein describe the effects of dative directing groups on the mechanism of the alkyne hydroamination.

Understanding the role of dative directing groups in Ti-catalyzed alkyne hydroamination

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.