2015•Organic LettersRequires access

Expanding the Forefront of Strong Organic Brønsted Acids: Proton-Catalyzed Hydroamination of Unactivated Alkenes and Activation of Au(I) for Alkyne Hydroamination

Roya Mirabdolbaghi, Travis Dudding

Abstract

The synthesis of a solid, bench-stable, strong organic Brønsted acid with a computed pKa of 0.9 is reported. An X-ray crystal structure and DFT calculations are provided which offer insight into the bonding of this acid. The application of this strong organic Brønsted acid as a catalyst for the intermolecular hydroamination of unactivated alkenes and as an activator for Au(I)-catalyzed alkyne hydroamination with anilines is described.

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Key concepts: Hydroamination, Chemistry, Alkyne, Brønsted–Lowry acid–base theory, Catalysis, Organic synthesis, Intermolecular force, Markovnikov's rule