Sequential One-Pot Synthesis of 3-Arylbenzofurans from N-Tosylhydrazones and Bromophenol Derivatives

被引：5

作者：

Lamaa, Diana ^{[1
]}

Hauguel, Camille ^{[1
]}

Lin, Hsin-Ping ^{[1
]}

Messe, Estelle ^{[1
]}

Gandon, Vincent ^{[2
,3
]}

Alami, Mouad ^{[1
]}

Hamze, Abdallah ^{[1
]}

机构：

[1] Univ Paris Saclay, BioCIS, CNRS, F-92290 Chatenay Malabry, France

[2] Univ Paris Saclay, Inst Chim Mol & Mat Orsay ICMMO, CNRS UMR 8182, F-91405 Orsay, France

[3] Inst Polytech Paris, Lab Chim Mol LCM, Ecole Polytech, CNRS UMR 9168, F-91128 Palaiseau, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 21期

关键词：

Catalysis;

D O I：

10.1021/acs.joc.0c01835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga-Valdes cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp(2)-Csp(2) and O-Csp(2) bonds. 3-Arylated benzofurans bearing various substituents were obtained with good to excellent yields (up to 90%). Mechanistic investigation strongly supports a radical process for the cyclization step.

引用

页码：13664 / 13673

页数：10

共 50 条

[1] One-Pot Multistep Synthesis of Trisubstituted Alkenes from N-Tosylhydrazones and Alcohols
Sha, Qiang
Wei, Yunyang
SYNTHESIS-STUTTGART, 2014, 46 (17): : 2353 - 2361
[2] One-Pot Selective Functionalization of Nitrogen-Containing Heterocycles with N-tosylhydrazones and Amines
Naret, Timothee
Bzeih, Tourin
Retailleau, Pascal
Alami, Mouad
Hamze, Abdallah
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (03) : 584 - 594
[3] One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines
Sha, Qiang
Wei, Yun-Yang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (34) : 5615 - 5620
[4] One-Step Synthesis of Sulfonamides from N-Tosylhydrazones
Tsai, Andy S.
Curto, John M.
Rocke, Benjamin N.
Dechert-Schmitt, Anne-Marie R.
Ingle, Gajendrasingh K.
Mascitti, Vincent
ORGANIC LETTERS, 2016, 18 (03) : 508 - 511
[5] One-Step Synthesis of Sulfonamides from N-Tosylhydrazones
Tsai, Andy
Curto, John
Rocke, Benjamin N.
Schmitt, Anne-Marie Dechert
Ingle, Gajendra
Mascitti, Vincent
SYNLETT, 2016, 27 (08) : A73 - A75
[6] Copper-catalyzed sulfonylation of N-tosylhydrazones followed by a one-pot C-N bond formation
Zhang, Kena
Provot, Olivier
Tran, Christine
Alami, Mouad
Hamze, Abdallah
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (24) : 5358 - 5367
[7] Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones
Li, Pan
Zhao, Jingjing
Wu, Chunrui
Larock, Richard C.
Shi, Feng
ORGANIC LETTERS, 2011, 13 (13) : 3340 - 3343
[8] One-Pot Synthesis of Azanucleosides from Proline Derivatives - Stereoselectivity in Sequential Processes
Boto, Alicia
Hernandez, Dacia
Hernandez, Rosendo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (20) : 3847 - 3857
[9] One-pot sequential synthesis of acetoxylated [60]fullerene derivatives
Chen, ZX
Wang, GW
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06): : 2380 - 2383
[10] Synthesis of 9-biarylfluorenes by one-pot, three-step reactions of N-tosylhydrazones, p-bromobenzeneboronic acid, and arylboronic acids
He, Jing
Zhang, Jie
Dai, Bin
Liu, Ping
JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (7-8) : 268 - 273

← 1 2 3 4 5 →