Ruthenium-CatalyzedRemote Trifunctionalization ofNon-Activated Alkenes via Cyano Migration and <i>meta</i>-C(sp<sup>2</sup>)–H Functionalization

A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy of remote cyano group migration and <i>meta</i>-C(sp<sup>2</sup>)–H functionalization. Through remote cyano migration, the alkenyl moiety undergoes difunctionalization to the formation of a benzylic radical intermediate. This intermediate facilitates <i>para</i>-selective C–H bond addition relative to the C–Ru bond within the Ru(III) complex, ultimately enabling trifunctionalization. This methodology provides an efficient route to a diverse array of nitrile-containing compounds with broad functional group compatibility.

Publication Details

Journal
Figshare
Published
2025-01-28
DOI
https://doi.org/10.1021/acs.orglett.4c04445.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Ruthenium-CatalyzedRemote Trifunctionalization ofNon-Activated Alkenes via Cyano Migration and meta-C(sp2)–H Functionalization

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Mycorrhizal Fungi and Plant Interactions
article

Ruthenium-CatalyzedRemote Trifunctionalization ofNon-Activated Alkenes via Cyano Migration and meta-C(sp2)–H Functionalization

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Abstract

A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy of remote cyano group migration and <i>meta</i>-C(sp<sup>2</sup>)–H functionalization. Through remote cyano migration, the alkenyl moiety undergoes difunctionalization to the formation of a benzylic radical intermediate. This intermediate facilitates <i>para</i>-selective C–H bond addition relative to the C–Ru bond within the Ru(III) complex, ultimately enabling trifunctionalization. This methodology provides an efficient route to a diverse array of nitrile-containing compounds with broad functional group compatibility.

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Mycorrhizal Fungi and Plant Interactions
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Ruthenium-CatalyzedRemote Trifunctionalization ofNon-Activated Alkenes via Cyano Migration and <i>meta</i>-C(sp<sup>2</sup>)–H Functionalization · Figshare (2025) | TGRS Research Map | TGRS