Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

Toshimasa Okita; Masaaki Komatsuda; Ami N. Saito; Tomoya Hisada; Tomoaki T. Takahara; Keito P. Nakayama; Ryota Isshiki; Ryosuke Takise; Kei Muto; Junichiro Yamaguchi

doi:10.1002/ajoc.201800207

Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

Toshimasa Okita, Masaaki Komatsuda, Ami N. Saito, Tomoya Hisada, Tomoaki T. Takahara, Keito P. Nakayama, Ryota Isshiki, Ryosuke Takise, Kei Muto, Junichiro Yamaguchi^*

^*Corresponding author for this work

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

12 Citations (Scopus)

Abstract

A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a S_NAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.

Original language	English
Pages (from-to)	1358-1361
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201800207
Publication status	Published - 2018 Jul

Keywords

C−H activation
decarbonylation
dibenzofurans
ethers
palladium

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1002/ajoc.201800207

Cite this

@article{c610b20862e2465a9bd7d9d68471a306,

title = "Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters",

abstract = "A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a SNAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.",

keywords = "C−H activation, decarbonylation, dibenzofurans, ethers, palladium",

author = "Toshimasa Okita and Masaaki Komatsuda and Saito, {Ami N.} and Tomoya Hisada and Takahara, {Tomoaki T.} and Nakayama, {Keito P.} and Ryota Isshiki and Ryosuke Takise and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP18H04272, JP16H04148 (to J. Y.), and JP17K14453 (to K.M.), and a JSPS research fellowship for young scientists (to T. R.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurement. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jul,

doi = "10.1002/ajoc.201800207",

language = "English",

volume = "7",

pages = "1358--1361",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "7",

}

TY - JOUR

T1 - Dibenzofuran Synthesis

T2 - Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

AU - Okita, Toshimasa

AU - Komatsuda, Masaaki

AU - Saito, Ami N.

AU - Hisada, Tomoya

AU - Takahara, Tomoaki T.

AU - Nakayama, Keito P.

AU - Isshiki, Ryota

AU - Takise, Ryosuke

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP18H04272, JP16H04148 (to J. Y.), and JP17K14453 (to K.M.), and a JSPS research fellowship for young scientists (to T. R.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurement. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/7

Y1 - 2018/7

N2 - A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a SNAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.

AB - A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a SNAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.

KW - C−H activation

KW - decarbonylation

KW - dibenzofurans

KW - ethers

KW - palladium

UR - http://www.scopus.com/inward/record.url?scp=85049829690&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85049829690&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201800207

DO - 10.1002/ajoc.201800207

M3 - Article

AN - SCOPUS:85049829690

SN - 2193-5807

VL - 7

SP - 1358

EP - 1361

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 7

ER -

Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this