Diversification of the Renewable Furanic Platform via 5-(Chloromethyl)furfural-Based Carbon Nucleophiles.

5-(chloromethyl)furfural Darzens reaction Reformatsky reaction biobased products platform molecules

Journal

ChemSusChem
ISSN: 1864-564X
Titre abrégé: ChemSusChem
Pays: Germany
ID NLM: 101319536

Informations de publication

Date de publication:
07 Jan 2021
Historique:
received: 15 07 2020
revised: 16 09 2020
pubmed: 18 9 2020
medline: 18 9 2020
entrez: 17 9 2020
Statut: ppublish

Résumé

Biobased 5-(chloromethyl)furoate and 5-methylfuroate esters can be deprotonated to function as furylogous lithium enolates, and the former can also undergo zinc insertion to access Reformatsky-type chemistry. Carbon nucleophilicity represents hitherto little-explored reactivity in these key carbohydrate-derived platform molecules, expanding their synthetic utility and potentially opening up new sustainable product markets (e. g., in epoxy resins or biobased dyes).

Identifiants

pubmed: 32941679
doi: 10.1002/cssc.202001718
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

303-305

Informations de copyright

© 2020 Wiley-VCH GmbH.

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Auteurs

Haoqian Miao (H)

Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California, 95616, USA.

Nikolay Shevchenko (N)

Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California, 95616, USA.

Andrew L Otsuki (AL)

Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California, 95616, USA.

Mark Mascal (M)

Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California, 95616, USA.

Classifications MeSH