Rhodium(<scp>iii</scp>)-catalyzed directed C–H naphthylation of aryl esters with 7-oxabenzonorbornadienes

A regioselective rhodium(III)-catalyzed C-H bond naphthylation of weak-coordinating aryl esters with bicyclic olefin compounds has been demonstrated. This present protocol is compatible with a variety of aryl esters as well as bicyclic olefins. The methodology produced highly valuable ester-functionalized 2-naphthylated products in good to excellent yields. A feasible reaction mechanism involving directing group assisted C-H activation was proposed and supported by competitive experiments and deuterium labelling studies.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc00692a
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Rhodium(iii)-catalyzed directed C–H naphthylation of aryl esters with 7-oxabenzonorbornadienes

N. Aravindan, Masilamani Jeganmohan
Chemical Communications
Catalytic C–H Functionalization Methods
article

Rhodium(iii)-catalyzed directed C–H naphthylation of aryl esters with 7-oxabenzonorbornadienes

N. Aravindan, Masilamani Jeganmohan
article en

Abstract

A regioselective rhodium(III)-catalyzed C-H bond naphthylation of weak-coordinating aryl esters with bicyclic olefin compounds has been demonstrated. This present protocol is compatible with a variety of aryl esters as well as bicyclic olefins. The methodology produced highly valuable ester-functionalized 2-naphthylated products in good to excellent yields. A feasible reaction mechanism involving directing group assisted C-H activation was proposed and supported by competitive experiments and deuterium labelling studies.

Chemical CommunicationsVol. 61(39)
Indian Institute of Technology Madras (IN)
Openalex Percentile: Top 94%
Catalytic C–H Functionalization Methods
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