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

4 Citations (Scopus)

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

Access to Document

10.1021/acs.orglett.1c01256

Cite this

@article{d0c3c0f9c6214152976b84d1c4842ed3,

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.",

year = "2021",

month = jun,

day = "4",

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

language = "English",

volume = "23",

pages = "4322--4326",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=85107713561&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85107713561&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c01256

DO - 10.1021/acs.orglett.1c01256

M3 - Article

C2 - 34029106

AN - SCOPUS:85107713561

VL - 23

SP - 4322

EP - 4326

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 11

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this