On the Valorisation of Chitin-Derived Furans by Milling

Author(s)

Mattioli, Renan Rodini ; Santos, Camila Souza ; de Souza, Bruna Butke ; Branco, Pedro Dominguez ; Bolt, Robert R. A. ; Raby-Buck, Sarah E. ; Cabral, Tadeu Luiz Gomes ; Tormena, Claudio F. ; Browne, Duncan L. ; Pastre, Julio C.

• Document type: Journal article
• Source: CHEMSUSCHEM; v. N/A, p. 6-pg., 2024-10-30.

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. (AU)

• FAPESP's process: 21/05081-5 - Chiral micelles for matrix-assisted DOSY
• Grantee: Tadeu Luiz Gomes Cabral
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 22/00774-5 - Employment of renewable chemical platforms to obtain synthetic intermediates with higher added-value.
• Grantee: Camila Souza Santos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 19/26450-9 - Application of green chemistry in Synhtesis of materials and building blocks employing renewable resources and continuous flow syntesis
• Grantee: Renan Rodini Mattioli
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 22/03872-8 - Mechanochemical synthesis of nitrogen-functionalized compounds obtained from biomass derivatives
• Grantee: Renan Rodini Mattioli
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 20/10246-0 - Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments
• Grantee: Claudio Francisco Tormena
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 21/06661-5 - Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Young Investigators Grants - Phase 2
• FAPESP's process: 23/01238-2 - Synthesis of new aromatic compounds derived from renewable sources
• Grantee: Bruna Butke de Souza
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 23/01232-4 - Exploring the benefits of enabling technologies in the synthesis of platform molecules
• Grantee: Pedro Dominguez Branco
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)