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.
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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26 September 2022
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
a84c2307-5cfd-4be4-9601-75d7bfab0148
Durandetti, Muriel
98edc796-722b-4237-bfb8-6fdbf2ac1891
Sebban, Muriel
dc6835fb-12d0-4a1a-a7d2-dd13d5045300
Hamdoun, Ghanem
4d295314-dcd0-4ff3-a842-f4de293da111
Oulyadi, Hassan
fa78fc84-2806-4a25-8675-3194c3d7a2ce
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Legros, Julien
0ad85dc7-e84f-4c8c-95a4-2aa46fbe89ec
Chataigner, Isabelle
13a550db-1647-4178-8200-f2547b148729
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), .
(doi:10.1039/D2CC04778K).
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.
Text
MS_DA_nitroarene_DD_HP
- Accepted Manuscript
More information
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
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Date deposited: 25 Nov 2022 17:39
Last modified: 17 Mar 2024 07:34
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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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