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High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes

High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes
High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes
Simple nitroarenes such as nitronaphthalenes and nitroquinolines smoothly undergo dearomatizing [4+2] cycloadditions with silyloxydienes under 16 kbar. Highly functionalized 3-dimensional polycyclic adducts bearing a tetrasubstituted carbon centre at the ring junction are obtained in one step from simple raw materials. This unprecedented dearomative Diels–Alder process is performed at room temperature without any chemical promoter, illustrating the exceptional role of high pressure as a physical promoter.
1359-7345
11807-11810
Rkein, Batoul
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Coffinier, Romain
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Powderly, Marian Elise
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Manneveau, Maxime
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Sanselme, Morgane
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Durandetti, Muriel
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Sebban, Muriel
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Hamdoun, Ghanem
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Oulyadi, Hassan
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Harrowven, David C.
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Legros, Julien
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Chataigner, Isabelle
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Rkein, Batoul
9eb68c71-a219-46b3-8a3a-7e43d50d4d8b
Coffinier, Romain
775e3d50-d4f7-42fd-9242-43758885d91b
Powderly, Marian Elise
6425ae48-d9ec-40e8-887e-e74b61137012
Manneveau, Maxime
b957b11d-389a-4466-8bc8-4be092561ecf
Sanselme, Morgane
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Durandetti, Muriel
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Sebban, Muriel
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Hamdoun, Ghanem
4d295314-dcd0-4ff3-a842-f4de293da111
Oulyadi, Hassan
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Harrowven, David C.
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Legros, Julien
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Chataigner, Isabelle
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Rkein, Batoul, Coffinier, Romain, Powderly, Marian Elise, Manneveau, Maxime, Sanselme, Morgane, Durandetti, Muriel, Sebban, Muriel, Hamdoun, Ghanem, Oulyadi, Hassan, Harrowven, David C., Legros, Julien and Chataigner, Isabelle (2022) High pressure promoted dearomatization of nitroarenes by [4+2] cycloadditions with silyloxydienes. Chemical Communications, 58 (84), 11807-11810. (doi:10.1039/D2CC04778K).

Record type: Article

Abstract

Simple nitroarenes such as nitronaphthalenes and nitroquinolines smoothly undergo dearomatizing [4+2] cycloadditions with silyloxydienes under 16 kbar. Highly functionalized 3-dimensional polycyclic adducts bearing a tetrasubstituted carbon centre at the ring junction are obtained in one step from simple raw materials. This unprecedented dearomative Diels–Alder process is performed at room temperature without any chemical promoter, illustrating the exceptional role of high pressure as a physical promoter.

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MS_DA_nitroarene_DD_HP - Accepted Manuscript
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Accepted/In Press date: 25 September 2022
Published date: 26 September 2022

Identifiers

Local EPrints ID: 472096
URI: http://eprints.soton.ac.uk/id/eprint/472096
ISSN: 1359-7345
PURE UUID: 7ffd424d-162c-4921-81cc-698face684e0
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 25 Nov 2022 17:39
Last modified: 06 Jun 2024 04:05

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Contributors

Author: Batoul Rkein
Author: Romain Coffinier
Author: Marian Elise Powderly
Author: Maxime Manneveau
Author: Morgane Sanselme
Author: Muriel Durandetti
Author: Muriel Sebban
Author: Ghanem Hamdoun
Author: Hassan Oulyadi
Author: Julien Legros
Author: Isabelle Chataigner

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