Ni‐Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross‐Coupling of Propargylic Acetates with Chlorohydrosilanes

Abstract This paper introduces an innovative strategy for the synthesis of multisubstituted allenes via nickel‐catalyzed reductive cross‐coupling reactions. The approach utilizes propargyl acetates and chlorosilanes to produce a variety of silyl‐substituted allenes. The reaction conditions are notably mild, and the process is characterized by high chemo‐ and regioselectivity, as well as an impressive substrate scope. Furthermore, the method can be readily extended to the use of chlorogermane and chlorostannane, facilitating the synthesis of germanium or stannium‐substituted allenes. This research not only offers a valuable strategy for the preparation of multisubstituted allenes but also significantly broadens the synthetic repertoire for the construction of highly functionalized molecules.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-12-12
DOI
https://doi.org/10.1002/ejoc.202401234
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.50
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article

Ni‐Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross‐Coupling of Propargylic Acetates with Chlorohydrosilanes

Hong Deng, Xiaohui Yan
2 citations
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.50
article

Ni‐Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross‐Coupling of Propargylic Acetates with Chlorohydrosilanes

Hong Deng, Xiaohui Yan
article en
2 citations

Abstract

Abstract This paper introduces an innovative strategy for the synthesis of multisubstituted allenes via nickel‐catalyzed reductive cross‐coupling reactions. The approach utilizes propargyl acetates and chlorosilanes to produce a variety of silyl‐substituted allenes. The reaction conditions are notably mild, and the process is characterized by high chemo‐ and regioselectivity, as well as an impressive substrate scope. Furthermore, the method can be readily extended to the use of chlorogermane and chlorostannane, facilitating the synthesis of germanium or stannium‐substituted allenes. This research not only offers a valuable strategy for the preparation of multisubstituted allenes but also significantly broadens the synthetic repertoire for the construction of highly functionalized molecules.

European Journal of Organic ChemistryVol. 28(7)
Huaibei Normal University (CN)
Clean water and sanitation
Openalex Percentile: Top 37%
Catalytic C–H Functionalization Methods
0.50
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