Biphenyl dicarboxylates from ethene and bifuran dimethyl esters

Ye, Mingchun; Kuo, Mi Jen; Lobo, Raul F.

doi:10.1016/j.mcat.2023.112949

Biphenyl dicarboxylates from ethene and bifuran dimethyl esters

Journal Article · Fri Jan 20 00:00:00 EST 2023 · Molecular Catalysis (Online)

DOI:https://doi.org/10.1016/j.mcat.2023.112949· OSTI ID:2419578

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Univ. of Delaware, Newark, DE (United States); Univ. of Delaware, Newark, DE (United States)
Univ. of Delaware, Newark, DE (United States)

The substrate scope of the Diels-Alder-Dehydration reaction was expanded to the deactivated bifuran structure. Dimethyl biphenyl-4,4'-dicarboxylate (1) and methyl 5- [4-(methoxycarbonyl)phenyl]-2-furoate (2) were synthesized from dimethyl 2,2'-bifuran-5,5'-dicarboxylate (3) via metal-triflate-catalyzed Diels-Alder-Dehydration reaction with ethene. A 31% yield of (1) was obtained using Sc(OTf)3 catalyst, and a 76.6% yield of (2) was obtained using La(OTf)3 catalyst under moderate reaction conditions. This approach is inherently selective to the 4,4'-dicarboxylates, and bypasses the methyl-group oxidation step of the dimethyl-biphenyl route.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Delaware, Newark, DE (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001004

OSTI ID:: 2419578

Journal Information:: Molecular Catalysis (Online), Journal Name: Molecular Catalysis (Online) Journal Issue: C Vol. 537; ISSN 2468-8231

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Biomass
Chemistry
Dehydration
Diels-Alder
Lewis acid catalyst
Metal triflate

Biphenyl dicarboxylates from ethene and bifuran dimethyl esters

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References (32)

Figures / Tables (4)

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Related Subjects