Employment of a C(sp<sup>3</sup>)-based nucleophile for photoinduced palladium-catalysed cross-coupling

The development of efficient methods for C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation remains a longstanding challenge in synthetic chemistry, especially in palladium catalysis employing sterically bulky electrophiles. In this study, we present a novel approach for achieving C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-coupling <i>via</i> photoinduced palladium catalysis, employing cyclopropanols as masked C(sp<sup>3</sup>)-nucleophiles. Leveraging the unique reactivity of photoexcited palladium, this protocol enables radical-mediated C(sp<sup>3</sup>)-C(sp<sup>3</sup>) coupling across a broad range of substrates including sterically hindered and functionally diverse alkyl halides under mild conditions. This method significantly expands the extent of palladium-catalysed cross-coupling for bond construction between sp<sup>3</sup>-hybridized carbon units, providing streamlined access to structurally complex C(sp<sup>3</sup>)-rich frameworks that are crucial for medicinal chemistry.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc02325d
Citations
3
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

Employment of a C(sp3)-based nucleophile for photoinduced palladium-catalysed cross-coupling

D. KIM, Byeongdo Roh, Bo-Sang Kim, Hong Geun Lee
3 citations
Chemical Science
Catalytic Cross-Coupling Reactions
2.81
article

Employment of a C(sp3)-based nucleophile for photoinduced palladium-catalysed cross-coupling

D. KIM, Byeongdo Roh, Bo-Sang Kim, Hong Geun Lee
article en
3 citations

Abstract

The development of efficient methods for C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation remains a longstanding challenge in synthetic chemistry, especially in palladium catalysis employing sterically bulky electrophiles. In this study, we present a novel approach for achieving C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-coupling <i>via</i> photoinduced palladium catalysis, employing cyclopropanols as masked C(sp<sup>3</sup>)-nucleophiles. Leveraging the unique reactivity of photoexcited palladium, this protocol enables radical-mediated C(sp<sup>3</sup>)-C(sp<sup>3</sup>) coupling across a broad range of substrates including sterically hindered and functionally diverse alkyl halides under mild conditions. This method significantly expands the extent of palladium-catalysed cross-coupling for bond construction between sp<sup>3</sup>-hybridized carbon units, providing streamlined access to structurally complex C(sp<sup>3</sup>)-rich frameworks that are crucial for medicinal chemistry.

Chemical ScienceVol. 16(27)
Seoul National University (KR)
National Research Foundation, National Research Foundation of Korea, Ministry of Science and ICT, South Korea
Openalex Percentile: Top 10%
Catalytic Cross-Coupling Reactions
2.81
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Employment of a C(sp<sup>3</sup>)-based nucleophile for photoinduced palladium-catalysed cross-coupling — D. KIM, Byeongdo Roh, et al. · Chemical Science (2025) | TGRS Research Map | TGRS