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Diversification of the Renewable Furanic Platform via 5-(Chloromethyl)furfural-Based Carbon Nucleophiles
Haoqian Miao1, Nikolay Shevchenko1, Andrew L Otsuki1
1Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California, 95616, USA.
Abstract:
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).
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