Synthesis of Aryl Naphthoquinones and Maleimides <i>via</i> Pd(II)‐Catalyzed Template‐Assisted <i>m</i>−C(sp<sup>2</sup>)−H Functionalization Reaction

An efficient approach for the synthesis of substituted aryl naphthoquinones via a Pd(II)-catalyzed template-assisted m-C(sp<sup>2</sup>)-H bond functionalization reaction of arylmethane sulfonates have been demonstrated. The method involves usage of less expensive and abundant pharmacologically important scaffold naphthoquinone. A wide range of arylmethane sulfonates were examined and found to be compatible with the protocol. The protocol has also been further extended to the synthesis of various substituted aryl maleimide scaffolds. A plausible reaction mechanism has also been proposed to account for the selective distal m-C(sp<sup>2</sup>)-H bond functionalization reaction.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-08-12
DOI
https://doi.org/10.1002/chem.202402162
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.00

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article

Synthesis of Aryl Naphthoquinones and Maleimides via Pd(II)‐Catalyzed Template‐Assisted m−C(sp2)−H Functionalization Reaction

Ananya Dutta, Masilamani Jeganmohan
4 citations
Chemistry - A European Journal
Catalytic C–H Functionalization Methods
1.00
article

Synthesis of Aryl Naphthoquinones and Maleimides via Pd(II)‐Catalyzed Template‐Assisted m−C(sp2)−H Functionalization Reaction

Ananya Dutta, Masilamani Jeganmohan
article en
4 citations

Abstract

An efficient approach for the synthesis of substituted aryl naphthoquinones via a Pd(II)-catalyzed template-assisted m-C(sp<sup>2</sup>)-H bond functionalization reaction of arylmethane sulfonates have been demonstrated. The method involves usage of less expensive and abundant pharmacologically important scaffold naphthoquinone. A wide range of arylmethane sulfonates were examined and found to be compatible with the protocol. The protocol has also been further extended to the synthesis of various substituted aryl maleimide scaffolds. A plausible reaction mechanism has also been proposed to account for the selective distal m-C(sp<sup>2</sup>)-H bond functionalization reaction.

Chemistry - A European JournalVol. 30(59)
Indian Institute of Technology Madras (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Indian Institute of Technology Madras, Science and Engineering Research Board
Openalex Percentile: Top 27%
Catalytic C–H Functionalization Methods
1.00
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Synthesis of Aryl Naphthoquinones and Maleimides <i>via</i> Pd(II)‐Catalyzed Template‐Assisted <i>m</i>−C(sp<sup>2</sup>)−H Functionalization Reaction — Ananya Dutta, Masilamani Jeganmohan · Chemistry - A European Journal (2024) | TGRS Research Map | TGRS