Rh(III)-Catalyzed\nAlkene <i>Anti</i> Nucleoamidation\nto Access Diverse Heterocycles

Alkene difunctionalization methods are an attractive\nway to rapidly\nbuild molecular complexity by using readily available starting materials.\nOne common approach is transition metal-catalyzed nucleometalation,\nwhich converts the C–C double bond to a C–Nu bond and\na C–M bond. Commonly, a tethered nucleophile is used to form\npharmaceutically relevant heterocyclic cores in this manner. The resulting\nalkylmetal species can then be further functionalized in a number\nof ways. While methods exist to aminate the C–M bond, direct\ninstallation of valuable amides is rare. Additionally, nucleometalation\nmethods are often limited to the use of a single type of nucleophile.\nHerein, we disclose a general method for the Rh­(III)-catalyzed nucleoamidation\nof alkenes, forming a variety of heterocyclic cores.

Publication Details

Journal
Figshare
Published
2024-11-04
DOI
https://doi.org/10.1021/acscatal.4c05499.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Rh(III)-Catalyzed\nAlkene Anti Nucleoamidation\nto Access Diverse Heterocycles

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Mycorrhizal Fungi and Plant Interactions
article

Rh(III)-Catalyzed\nAlkene Anti Nucleoamidation\nto Access Diverse Heterocycles

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Abstract

Alkene difunctionalization methods are an attractive\nway to rapidly\nbuild molecular complexity by using readily available starting materials.\nOne common approach is transition metal-catalyzed nucleometalation,\nwhich converts the C–C double bond to a C–Nu bond and\na C–M bond. Commonly, a tethered nucleophile is used to form\npharmaceutically relevant heterocyclic cores in this manner. The resulting\nalkylmetal species can then be further functionalized in a number\nof ways. While methods exist to aminate the C–M bond, direct\ninstallation of valuable amides is rare. Additionally, nucleometalation\nmethods are often limited to the use of a single type of nucleophile.\nHerein, we disclose a general method for the Rh­(III)-catalyzed nucleoamidation\nof alkenes, forming a variety of heterocyclic cores.

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Mycorrhizal Fungi and Plant Interactions
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