eprintid: 10204780
rev_number: 6
eprint_status: archive
userid: 699
dir: disk0/10/20/47/80
datestamp: 2025-02-17 11:22:15
lastmod: 2025-02-17 11:22:15
status_changed: 2025-02-17 11:22:15
type: article
metadata_visibility: show
sword_depositor: 699
creators_name: Mattioli, Renan Rodini
creators_name: Santos, Camila Souza
creators_name: de Souza, Bruna Butke
creators_name: Branco, Pedro Dominguez
creators_name: Bolt, Robert RA
creators_name: Raby-Buck, Sarah E
creators_name: Cabral, Tadeu Luiz Gomes
creators_name: Tormena, Claudio F
creators_name: Browne, Duncan L
creators_name: Pastre, Julio C
title: On the Valorisation of Chitin-Derived Furans by Milling
ispublished: pub
divisions: UCL
divisions: B02
divisions: C08
divisions: D10
divisions: G08
divisions: G09
keywords: Diels-Alder, Hydrazone, Aromatics, Chitin, Mechanochemistry
note: © 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).
abstract: Chitin-derived furans offer a sustainable alternative feedstock for nitrogen appended aromatic compounds. Herein, we address the challenge of using chitin-derived furans, 3-acetamido-5-acetylfuran (3A5AF) and 3-acetamido-5-furfural aldehyde (3A5F), to favour the formation of exo Diels–Alder adducts and 4-acetylaminophthalimides respectively, using a mechanochemical ball-milling technique. Mechanochemical activation is explored through the synthesis of 7-oxa-norbornene backbones with novel substitution pattern from 3A5AF in yields up to 77 % and improved exo:endo selectivity compared to solution-phase reactions. The synthesis of 4-acetylaminophthalimides from 3A5F in yields up to 79 % is also showcased from hydrazone derivatives.
date: 2025-02
date_type: published
publisher: WILEY-V C H VERLAG GMBH
official_url: https://doi.org/10.1002/cssc.202401584
oa_status: green
full_text_type: pub
language: eng
primo: open
primo_central: open_green
verified: verified_manual
elements_id: 2312581
doi: 10.1002/cssc.202401584
medium: Print-Electronic
lyricists_name: Browne, Duncan
lyricists_name: Bolt, Robert
lyricists_name: Raby Buck, Sarah
lyricists_id: DBROW94
lyricists_id: RRABO93
lyricists_id: SRABY05
actors_name: Browne, Duncan
actors_name: Harris, Jean
actors_id: DBROW94
actors_id: JAHAR68
actors_role: owner
actors_role: impersonator
funding_acknowledgements: 2019/26450-9 [Sao Paulo Research Foundation-FAPESP]; 2022/03872-8 [Sao Paulo Research Foundation-FAPESP]; 2022/00774-5 [Sao Paulo Research Foundation-FAPESP]; 2023/01238-2 [Sao Paulo Research Foundation-FAPESP]; 2023/01232-4 [Sao Paulo Research Foundation-FAPESP]; 2021/05081-5 [Sao Paulo Research Foundation-FAPESP]; 2020/10246-0 [Sao Paulo Research Foundation-FAPESP]; 2021/06661-5 [Sao Paulo Research Foundation-FAPESP]; 308540/2021-2 [Brazilian National Council for Scientific and Technological Development-CNPq]; 001 [Coordination for the Improvement of Higher Education Personnel-CAPES]; 2023-01238 [Formas]; 2023-01238 [Forte]; 2022-03872 [Vinnova]
full_text_status: public
publication: ChemSusChem
volume: 18
number: 3
article_number: e202401584
pages: 6
event_location: Germany
citation:        Mattioli, Renan Rodini;    Santos, Camila Souza;    de Souza, Bruna Butke;    Branco, Pedro Dominguez;    Bolt, Robert RA;    Raby-Buck, Sarah E;    Cabral, Tadeu Luiz Gomes;             ... Pastre, Julio C; + view all <#>        Mattioli, Renan Rodini;  Santos, Camila Souza;  de Souza, Bruna Butke;  Branco, Pedro Dominguez;  Bolt, Robert RA;  Raby-Buck, Sarah E;  Cabral, Tadeu Luiz Gomes;  Tormena, Claudio F;  Browne, Duncan L;  Pastre, Julio C;   - view fewer <#>    (2025)    On the Valorisation of Chitin-Derived Furans by Milling.                   ChemSusChem , 18  (3)    , Article e202401584.  10.1002/cssc.202401584 <https://doi.org/10.1002/cssc.202401584>.       Green open access   
 
document_url: https://discovery.ucl.ac.uk/id/eprint/10204780/1/ChemSusChem_2024.pdf