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

被引：15

作者：

Okita, Toshimasa ^{[1
]}

Komatsuda, Masaaki ^{[1
]}

Saito, Ami N. ^{[1
]}

Hisada, Tomoya ^{[1
]}

Takahara, Tomoaki T. ^{[1
]}

Nakayama, Keito P. ^{[1
]}

Isshiki, Ryota ^{[1
]}

Takise, Ryosuke ^{[2
]}

Muto, Kei ^{[1
]}

Yamaguchi, Junichiro ^{[1
]}

机构：

[1] Waseda Univ, Dept Appl Chem, Shinjuku Ku, 3-4-1 Ohkubo, Tokyo 1698555, Japan

[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 07期

关键词：

C-H activation; decarbonylation; dibenzofurans; ethers; palladium; POLYOXYGENATED DIBENZOFURANS; ARYLBORONIC ACIDS; NICKEL CATALYSIS; ALPHA-ARYLATION; ARYL CHLORIDES; CYCLIZATION; DERIVATIVES; ACTIVATION; HETEROCYCLES; OLEFINATION;

D O I：

10.1002/ajoc.201800207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1358 / 1361

页数：4

共 50 条

[1] Pd-Catalyzed Decarbonylative C-H Coupling of Azoles and Aromatic Esters
Matsushita, Kaoru
Takise, Ryosuke
Hisada, Tomoya
Suzuki, Shin
Isshiki, Ryota
Itami, Kenichiro
Muto, Kei
Yamaguchi, Junichiro
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2393 - 2396
[2] Rhodium-Catalyzed Decarbonylative C-H Arylation of 2-Aryloxybenzoic Acids Leading to Dibenzofuran Derivatives
Maetani, Shinji
Fukuyama, Takahide
Ryu, Ilhyong
ORGANIC LETTERS, 2013, 15 (11) : 2754 - 2757
[3] Photothermally induced decarbonylative C-H arylation of arenes with aldehydes
Lin, Zhenyuan
Wang, Huahui
Wu, Qinghua
Lin, Junxuan
Guo, Xucong
Chen, Manqi
Chen, Lu
Li, Yibiao
Shen, Chengshuo
Zhang, Min
JOURNAL OF CATALYSIS, 2023, 426 : 96 - 100
[4] Direct Synthesis of K-Region Functionalized Polycyclic Aromatic Hydrocarbons via Twofold Intramolecular C-H/C-H Arylation
Li, Hao
Lu, Dandan
Qian, Bai-Yang
Lin, Jianbin
Zhang, Hui-Jun
ORGANIC LETTERS, 2024, 26 (51) : 11140 - 11144
[5] Pd-Catalyzed Denitrative Intramolecular C-H Arylation
Asahara, Kitty K.
Okita, Toshimasa
Saito, Ami N.
Muto, Kei
Nakao, Yoshiaki
Yamaguchi, Junichiro
ORGANIC LETTERS, 2019, 21 (12) : 4721 - 4724
[6] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
Amaike, Kazuma
Muto, Kei
Yamaguchi, Junichiro
Itami, Kenichiro
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13573 - 13576
[7] C-H Arylation in the Synthesis of π-Conjugated Polymers
Suraru, Sabin-Lucian
Lee, Jason A.
Luscombe, Christine K.
ACS MACRO LETTERS, 2016, 5 (06): : 724 - 729
[8] Synthesis of Indolines by Copper-Mediated Intramolecular Aromatic C-H Amination
Takamatsu, Kazutaka
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06): : 3242 - 3249
[9] Direct arylation of aromatic C-H bond catalyzed by phthalocyanine
Gai, Lizhi
To, Ching Tat
Chan, Kin Shing
TETRAHEDRON LETTERS, 2014, 55 (46) : 6373 - 6376
[10] Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KOtBu promoted intramolecular C-H arylation
Sharma, Sushila
Kumar, Manoranjan
Sharma, Shruti
Nayal, Onkar S.
Kumar, Neeraj
Singh, Bikram
Sharma, Upendra
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (36) : 8536 - 8544

← 1 2 3 4 5 →