Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes

The first Cu-catalyzed dehydrogenative C–O cyclization for the synthesis of furan-fused thienoacenes is described. A variety of heteroacenes including a thieno­[3,2-b]­furan or a thieno­[2,3-b]­furan skeleton were synthesized by intramolecular C–H/O–H coupling. The use of a mixed solvent of N-methyl...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 11; pp. 4322 - 4326
Main Authors Mitsudo, Koichi, Kobashi, Yoshiaki, Nakata, Kaito, Kurimoto, Yuji, Sato, Eisuke, Mandai, Hiroki, Suga, Seiji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.06.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The first Cu-catalyzed dehydrogenative C–O cyclization for the synthesis of furan-fused thienoacenes is described. A variety of heteroacenes including a thieno­[3,2-b]­furan or a thieno­[2,3-b]­furan skeleton were synthesized by intramolecular C–H/O–H coupling. The use of a mixed solvent of N-methyl-2-pyrrolidone, ethylene glycol monomethyl ether, and toluene was essential for suppressing side reactions and efficiently promoting the reaction. Double C–O cyclization was also conducted to afford highly π-expanded furan-fused thienoacenes.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01256