Palladium-catalyzed intramolecular oxypalladation-initiated cascade: solvent-dependent chemodivergent approach to functionalized benzazepines and tetrahydroquinolines

Anish Gupta; Tanvi Jandial; Muthu Karuppasamy; Nattamai Bhuvanesh; Subbiah Nagarajan; C. Uma Maheswari; Vellaisamy Sridharan

doi:10.1039/D3CC01370G

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Palladium-catalyzed intramolecular oxypalladation-initiated cascade: solvent-dependent chemodivergent approach to functionalized benzazepines and tetrahydroquinolines†

Anish Gupta,

^a Tanvi Jandial,^a Muthu Karuppasamy,^a Nattamai Bhuvanesh,^b Subbiah Nagarajan,

^c C. Uma Maheswari

^d and Vellaisamy Sridharan

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu, JK, India
E-mail: vesridharan@gmail.com, sridharan.che@cujammu.ac.in

^b Department of Chemistry, Texas A & M University, College Station, Texas, USA

^c Department of Chemistry, National Institute of Technology, Warangal, Warangal, Telangana, India

^d Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur, Tamil Nadu, India

Abstract

Palladium-catalyzed, solvent-dependent intramolecular oxypalladation-triggered domino sequences of internal alkynes bearing tethered nucleophilic carboxylic ester and electrophilic enone functionalities were developed for the chemodivergent synthesis of two completely distinct biologically significant complex molecules including isochromenone-fused benzazepines and isobenzofuranone-fused tetrahydroquinolines/chromanes in a single synthetic operation.

This article is part of the themed collection: 2022 CRSI Medal Winners Collection

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DOI: https://doi.org/10.1039/D3CC01370G
Article type: Communication
Submitted: 20 Mar 2023
Accepted: 30 Mar 2023
First published: 30 Mar 2023

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Chem. Commun., 2023,59, 5233-5236

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Palladium-catalyzed intramolecular oxypalladation-initiated cascade: solvent-dependent chemodivergent approach to functionalized benzazepines and tetrahydroquinolines

A. Gupta, T. Jandial, M. Karuppasamy, N. Bhuvanesh, S. Nagarajan, C. U. Maheswari and V. Sridharan, Chem. Commun., 2023, 59, 5233 DOI: 10.1039/D3CC01370G

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Chemical Communications

Palladium-catalyzed intramolecular oxypalladation-initiated cascade: solvent-dependent chemodivergent approach to functionalized benzazepines and tetrahydroquinolines†

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Palladium-catalyzed intramolecular oxypalladation-initiated cascade: solvent-dependent chemodivergent approach to functionalized benzazepines and tetrahydroquinolines

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