pH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water

Abstract

Amination of allylic alcohols is an effective approach in the facile synthesis of <i>N</i>-allylic alkylation or <i>N</i>-alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typically limited to achieve either <i>N</i>-allylic alkylation or <i>N</i>-alkylation products via a certain catalyst. In this article, a pH-mediated selective synthesis of <i>N</i>-allylic alkylation or <i>N</i>-alkylation amines with allylic alcohols via an iridium catalyst with water as the environmental benign solvent is revealed, enabling the miscellaneous synthesis of <i>N</i>-allylic alkylation and <i>N</i>-alkylation products in outstanding yields. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access a distinct entry for the synthesis of the antifungal drug naftifine.