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The Piancatelli Reaction and its Variants: Recent Applications to High Added-Value Chemicals and Biomass Valorization

Abstract

The Piancatelli reaction, also called Piancatelli rearrangement, consists in the direct conversion of furfuryl alcohols in cyclopentenone derivatives through a furan ring opening-electrocyclization process. Following its discovery in the late 70’s, this reaction has been scarcely used for more than 40 years, but recently focused a particular interest from the scientific community and an increasing number of publications on the topic has emerged in the last few years. The first part of this review provides an overview of the recent achievement in classical Piancatelli reactions, discussing reaction conditions and catalytic systems, whereas a second part focuses on the variants recently developed, including the use of new nucleophiles in the process. Finally, the third part of this review deals with the recent applications of this transformation to the production of commodity chemicals from renewable carbon feedstock based on sugar-derived furanic platforms.

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Publication details

The article was received on 01 Dec 2017, accepted on 10 Jan 2018 and first published on 10 Jan 2018


Article type: Review Article
DOI: 10.1039/C7OB02962D
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    The Piancatelli Reaction and its Variants: Recent Applications to High Added-Value Chemicals and Biomass Valorization

    C. Verrier, S. Moebs-Sanchez, Y. Queneau and F. Popowycz, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7OB02962D

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