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

Nianhua Luo, Yuhong Zhong, Hongling Shui, Renshi Luo

2021The Journal of Organic Chemistry32 citationsDOI

Abstract

Amination of allylic alcohols is an effective approach in the facile synthesis of N-allylic alkylation or N-alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typically limited to achieve either N-allylic alkylation or N-alkylation products via a certain catalyst. In this article, a pH-mediated selective synthesis of N-allylic alkylation or N-alkylation amines with allylic alcohols via an iridium catalyst with water as the environmental benign solvent is revealed, enabling the miscellaneous synthesis of N-allylic alkylation and N-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.

Topics & Concepts

AlkylationChemistryTsuji–Trost reactionAminationAllylic rearrangementCatalysisCombinatorial chemistryIridiumOrganic chemistrySolventAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisOrganoboron and organosilicon chemistry
pH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water | Litcius