Iodide Anion Enables a Reductive Cross‐Electrophile Coupling for Preparing Tertiary Amines

The reducing power of iodide anion is an underexplored property that can be used for the cross-electrophile coupling of organic molecules. Herein we harness this trait for the preparation of tertiary amines through the combination of two simple reagents: an electrophilic-carbon precursor and an iminium iodide in a dual role - both as nitrogen-containing building block and as reducing agent. The underlying mechanism of this new C-C bond-formation paradigm is explored through a combination of experiment and quantum chemical calculations.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-11-19
DOI
https://doi.org/10.1002/anie.202409688
Citations
3
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Iodide Anion Enables a Reductive Cross‐Electrophile Coupling for Preparing Tertiary Amines

Miran Lemmerer, Boris Maryasin, Daniel Kaiser, David Just et al.
3 citations
Angewandte Chemie International Edition
Catalytic Cross-Coupling Reactions
0.75
article

Iodide Anion Enables a Reductive Cross‐Electrophile Coupling for Preparing Tertiary Amines

Miran Lemmerer, Boris Maryasin, Daniel Kaiser, David Just, Veronica Tona, Andreas B. zur Bonsen, Giovanni Di Mauro, Nuno Maulide, Miloš Vavrík
article en
3 citations

Abstract

The reducing power of iodide anion is an underexplored property that can be used for the cross-electrophile coupling of organic molecules. Herein we harness this trait for the preparation of tertiary amines through the combination of two simple reagents: an electrophilic-carbon precursor and an iminium iodide in a dual role - both as nitrogen-containing building block and as reducing agent. The underlying mechanism of this new C-C bond-formation paradigm is explored through a combination of experiment and quantum chemical calculations.

Angewandte Chemie International EditionVol. 64(2)
University of Vienna (AT)
Austrian Science Fund, Universität Wien
Openalex Percentile: Top 31%
Catalytic Cross-Coupling Reactions
0.75
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Iodide Anion Enables a Reductive Cross‐Electrophile Coupling for Preparing Tertiary Amines — Miran Lemmerer, Boris Maryasin, et al. · Angewandte Chemie International Edition (2024) | TGRS Research Map | TGRS