Pd‐Catalyzed Skeletal Rearrangement via C(<i>sp</i><sup>3</sup>)−C(<i>sp</i><sup>3</sup>) Activation to Access <i>α</i>,<i>β</i>‐Unsaturated <i>δ</i>/<i>γ</i>‐Lactone

Abstract The activation of non‐polar aliphatic C−C bonds represents a significant challenge that remains to be addressed in the field of Pd(II) catalysis. In this study, we present a dual ligand approach as a means of addressing this issue. The process entails lactonization of cyclobutane and cyclopropane carboxylic acid via the activation of non‐polar C( sp 3 )−C( sp 3 ) bond despite the high feasibility of both οrtho ‐C( sp 2 )−H and β or γ ‐C( sp 3 )−H activation. Density Functional Theory (DFT) calculations were performed to reveal the mechanistic insights and elucidate the role of dual ligands in facilitating this challenging transformation.

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Publication Details

Journal
Angewandte Chemie
Published
2025-02-04
DOI
https://doi.org/10.1002/ange.202423175
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Pd‐Catalyzed Skeletal Rearrangement via C(sp3)−C(sp3) Activation to Access α,β‐Unsaturated δ/γ‐Lactone

Kartic Manna, Puneet Gupta, Nikunj Kumar, Akhilesh K. Sharma et al.
Angewandte Chemie
Catalytic C–H Functionalization Methods
article

Pd‐Catalyzed Skeletal Rearrangement via C(sp3)−C(sp3) Activation to Access α,β‐Unsaturated δ/γ‐Lactone

Kartic Manna, Puneet Gupta, Nikunj Kumar, Akhilesh K. Sharma, Debabrata Maiti, Suman Maji
article en

Abstract

Abstract The activation of non‐polar aliphatic C−C bonds represents a significant challenge that remains to be addressed in the field of Pd(II) catalysis. In this study, we present a dual ligand approach as a means of addressing this issue. The process entails lactonization of cyclobutane and cyclopropane carboxylic acid via the activation of non‐polar C( sp 3 )−C( sp 3 ) bond despite the high feasibility of both οrtho ‐C( sp 2 )−H and β or γ ‐C( sp 3 )−H activation. Density Functional Theory (DFT) calculations were performed to reveal the mechanistic insights and elucidate the role of dual ligands in facilitating this challenging transformation.

Angewandte ChemieVol. 137(11)
Indian Institute of Technology Roorkee (IN), Indian Institute of Technology Bombay (IN)
Openalex Percentile: Top 98%
Catalytic C–H Functionalization Methods
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