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

Koichi Mitsudo; Yoshiaki Kobashi; Kaito Nakata; Yuji Kurimoto; Eisuke Sato; Hiroki Mandai; Seiji Suga

doi:10.1021/acs.orglett.1c01256

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

Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	4322-4326
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.1c01256
Publication status	Published - Jun 4 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c01256

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title = "Cu-Catalyzed Dehydrogenative C-O Cyclization for the Synthesis of Furan-Fused Thienoacenes",

abstract = "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. ",

author = "Koichi Mitsudo and Yoshiaki Kobashi and Kaito Nakata and Yuji Kurimoto and Eisuke Sato and Hiroki Mandai and Seiji Suga",

note = "Funding Information: This work was supported in part by JSPS KAKENHI grant numbers JP19K05477, JP19K05478, and JP18H04455 for Middle Molecular Strategy and by JST, ACT-C, Japan. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c01256",

language = "English",

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journal = "Organic Letters",

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T1 - Cu-Catalyzed Dehydrogenative C-O Cyclization for the Synthesis of Furan-Fused Thienoacenes

AU - Mitsudo, Koichi

AU - Kobashi, Yoshiaki

AU - Nakata, Kaito

AU - Kurimoto, Yuji

AU - Sato, Eisuke

AU - Mandai, Hiroki

AU - Suga, Seiji

N1 - Funding Information: This work was supported in part by JSPS KAKENHI grant numbers JP19K05477, JP19K05478, and JP18H04455 for Middle Molecular Strategy and by JST, ACT-C, Japan. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/6/4

Y1 - 2021/6/4

N2 - 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.

AB - 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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JO - Organic Letters

JF - Organic Letters

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ER -

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

Abstract

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