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. 2024 Feb 6;60(12):1615-1618.
doi: 10.1039/d3cc05594a.

Iridium-catalysed hydroamination of internal homoallylic amines

An T Ho  1 , Evan P Vanable  2 , Chelsea San Miguel  1 , Kami L Hull  1   2
Affiliations

Iridium-catalysed hydroamination of internal homoallylic amines

An T Ho et al. Chem Commun (Camb). .

Abstract

An Ir-catalysed regioselective hydroamination of internal homoallylic amines is reported. Both cyclic and acyclic internal olefins undergo directed hydroamination reactions with both aromatic and cyclic aliphatic amines to afford a variety of 1,4-diamines in fair to excellent yields. Diastereoselectivity and mechanistic investigations support that for cyclic substrates the reactions are proceeding via trans-aminoiridation to form a 5-membered metalacyclic intermediate.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Hydroamination of internal olefins.
Scheme 2
Scheme 2. Scope of hydroamination with anilines.
Scheme 3
Scheme 3. Scope of hydroamination with aliphatic amines.
Scheme 4
Scheme 4. Mechanistic investigation.
See this image and copyright information in PMC

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