Zinc/Bismuth-Mediated Allylation Reaction of Biomass Feedstocks: Synthesis of Furanic Diols

This paper is dedicated to Prof. Dennis Curran on the occasion of his 70^th birthday.

Abstract

Biomass-based diols have been synthesized by a Zn/Bi-mediated Barbier-type of reaction from furanic aldehydes and allyl halides to access allylated diols. The allylated diols can be readily converted into alkylated diols by hydrogenation. These furanic diols could be potential replacements for fossil fuel based bisphenol A (BPA) which has an adverse endocrine-disrupting effect on humans. This mild and green protocol provides symmetric and nonsymmetric diols in high yields. A chemoselective reduction of allylic double bonds provides diols with unique substitution.

Key words

bisphenol A - furanic diols - Barbier reaction - biomass - allylation - zinc - bismuth

Publication History

Received: 17 November 2023

Accepted after revision: 10 January 2024

Accepted Manuscript online:
10 January 2024

Article published online:
14 February 2024

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