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. 2022 Mar 4;87(5):3114-3122.
doi: 10.1021/acs.joc.1c02877. Epub 2022 Feb 22.

Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks

Jeymy T Sarmiento  1 , María Cárcel  1 , Carmen Ramírez de Arellano  1 , Teresa Varea  1 , Gregorio Asensio  1 , Andrea Olmos  1
Affiliations

Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks

Jeymy T Sarmiento et al. J Org Chem. .

Abstract

α-Chloromethylketimines have been obtained through a gold-catalyzed hydroamination of aromatic and aliphatic 1-chloroalkynes with aromatic amines by using equimolar amounts of both reagents. This procedure has allowed the preparation and spectroscopic characterization of α-chloromethylketimines for the first time with a high degree of purity, complete conversion, and atom economy. The synthetic usefulness of the methodology has been demonstrated with the preparation of β-chloroamines and indoles.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Syntheses of Halomethylketimines
Scheme 2
Scheme 2. Synthesis of α-Chloroimine Tautomers 3ea and 3eb
Figure 1
Figure 1
Synthesis and 1H NMR spectrum of chloroimine 3bb.
Figure 2
Figure 2
NMR monitoring of gold-catalyzed 3da formation.
See this image and copyright information in PMC

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