Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans

被引：4

作者：

Aggarwal, Sakshi ^{[1
]}

Srinivas, Dasari ^{[1
]}

Sreenivasulu, Chinnabattigalla ^{[1
]}

Satyanarayana, Gedu ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Hyderabad 502285, Telangana, India

来源：

RSC ADVANCES | 2020年 / 10卷 / 37期

关键词：

ONE-POT SYNTHESIS; MARINE SPONGE; BIOLOGICAL-ACTIVITY; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; O-ALKYNYLPHENOLS; FACILE SYNTHESIS; ALKENYL PHENOLS; C-C; MICROWAVE;

D O I：

10.1039/d0ra03071f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recent research has been focused on the transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans fromortho-alkenyl phenolsviaintramolecular dehydrogenative coupling. Notably, simple O(2)gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.

引用

页码：22264 / 22272

页数：9

共 82 条

[1]

Adams R., 1956, J AM CHEM SOC, V78, P8

[2] Orthogonal selectivity with cinnamic acids in 3-substituted benzofuran synthesis through C-H olefination of phenols [J].

Agasti, Soumitra ;

Sharma, Upendra ;

Naveen, Togati ;

Maiti, Debabrata .

CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5375-5378

[3] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].

Anderson, Kevin W. ;

Ikawa, Takashi ;

Tundel, Rachel E. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695

[4] Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT1 and/or BLT2 inhibitory activities [J].

Ando, Kumiko ;

Kawamura, Yoko ;

Akai, Yukiko ;

Kunitomo, Jun-ichi ;

Yokomizo, Takehiko ;

Yamashita, Masayuki ;

Ohta, Shunsaku ;

Ohishi, Takahiro ;

Ohishi, Yoshitaka .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (02) :296-307

[5] Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].

Arcadi, A ;

Cacchi, S ;

DelRosario, M ;

Fabrizi, G ;

Marinelli, F .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288

[6] Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues [J].

Aslam, SN ;

Stevenson, PC ;

Phythian, SJ ;

Veitch, NC ;

Hall, DR .

TETRAHEDRON, 2006, 62 (17) :4214-4226

[7] Iron and Copper Salts in the Synthesis of Benzo[b]furans [J].

Bonnamour, Julien ;

Piedrafita, Maria ;

Bolm, Carsten .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1577-1581

[8]

Builla J. A., 2011, MOD HETEROCYCL CHEM, V1, P238

[9] REACTION OF ORTHO ALKENYL PHENOLS AND ALKYLPHENOLS WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (DDQ) - SYNTHESES OF 2,2-DIALKYLCHROMENES [J].

CARDILLO, G ;

CRICCHIO, R ;

MERLINI, L .

TETRAHEDRON, 1971, 27 (10) :1875-&

[10] Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone [J].

Carlsson, B ;

Singh, BN ;

Temciuc, M ;

Nilsson, S ;

Li, YL ;

Mellin, C ;

Malm, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :623-630

← 1 2 3 4 5 6 7 8 9 →