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Aluminosilicate-mediated C(sp2)–H alkylation of furans using allylic alcohols

Journal Article · · Catalysis Science and Technology
DOI:https://doi.org/10.1039/D4CY01320D· OSTI ID:2574160
 [1];  [2];  [1];  [1];  [1];  [1]
  1. Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
  2. Univ. of Oklahoma, Norman, OK (United States)
+ Show Author Affiliations
Alkyl furans have a variety of applications and therefore numerous approaches exist for their synthesis. While these methods can be effective, there are various drawbacks largely associated with the waste generated. Herein we report a novel method for the direct coupling of readily available furans with allylic alcohols. These include terpenoid alcohols such as geraniol and prenol, which are readily available from renewable, bio-derived feedstocks. Furthermore, the reaction is facilitated using aluminosilicates, including zeolites. It was found that Y-type zeolites were highly effective at mediating the coupling with furan, giving the 2-alkylated furan high yields. While various allylic alcohols were effective for this reaction, the identity of the furan proved to have a drastic impact on reactivity. For substituted furans, the reaction proved most effective with an amorphous aluminosilicate and calculations later revealed potential key factors in further developing and generalizing this methodology.
Research Organization:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Organization:
USDOE National Nuclear Security Administration (NNSA); USDOE Laboratory Directed Research and Development (LDRD) Program
Grant/Contract Number:
89233218CNA000001
OSTI ID:
2574160
Report Number(s):
LA-UR--24-20670; 10.1039/D4CY01320D; 2044-4761
Journal Information:
Catalysis Science and Technology, Journal Name: Catalysis Science and Technology Journal Issue: 15 Vol. 15; ISSN 2044-4761; ISSN 2044-4753
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY