Synthesis ofγ‑Lactams via Palladium-CatalyzedC(sp<sup>3</sup>)–H Bond Activation of Alkyl Sulfonamides withSubstituted Alkenes

A methodology for the <i>γ</i>-butyrolactam scaffolds via ligand-enabled C(sp<sup>3</sup>)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol has been found to be compatible with several activated and unactivated olefins, and the desired lactams were formed in excellent yields. A plausible mechanism has been described to account for the desired lactamization reaction as well as supported by mechanistic investigation including a <sup>1</sup>H NMR study and isolation of a palladacycle intermediate.

Publication Details

Journal
Figshare
Published
2025-02-20
DOI
https://doi.org/10.1021/acs.orglett.5c00152.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Synthesis ofγ‑Lactams via Palladium-CatalyzedC(sp3)–H Bond Activation of Alkyl Sulfonamides withSubstituted Alkenes

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Catalytic C–H Functionalization Methods
article

Synthesis ofγ‑Lactams via Palladium-CatalyzedC(sp3)–H Bond Activation of Alkyl Sulfonamides withSubstituted Alkenes

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Abstract

A methodology for the <i>γ</i>-butyrolactam scaffolds via ligand-enabled C(sp<sup>3</sup>)–H bond functionalization of sulfonamides with olefins has been demonstrated. The protocol has been found to be compatible with several activated and unactivated olefins, and the desired lactams were formed in excellent yields. A plausible mechanism has been described to account for the desired lactamization reaction as well as supported by mechanistic investigation including a <sup>1</sup>H NMR study and isolation of a palladacycle intermediate.

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Catalytic C–H Functionalization Methods
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Synthesis ofγ‑Lactams via Palladium-CatalyzedC(sp<sup>3</sup>)–H Bond Activation of Alkyl Sulfonamides withSubstituted Alkenes · Figshare (2025) | TGRS Research Map | TGRS