Copper-mediated N- and O-arylations with arylboronic acids in a continuous flow microreactor: a new avenue for efficient scalability

被引：31

作者：

Singh, Brajendra K. ^{[2
,3
]}

Stevens, Christian V. ^{[1
]}

Acke, Davy R. J. ^{[1
]}

Parmar, Virinder S. ^{[3
]}

Van der Eycken, Erik V. ^{[2
]}

机构：

[1] Univ Ghent, Res Grp SynBioC, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium

[2] Univ Louvain, Dept Chem, Lab Organ & Microwave Assisted chem, B-3001 Louvain, Belgium

[3] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 01期

关键词：

Copper-mediated; N-Arylation; O-Arylation; Arylboronic acid; Continuous flow; Microreactor; Scalability; C-N; CATALYZED SYNTHESIS; ARYL HALIDES; MICROWAVE; TECHNOLOGY; PHENOLS; REACTOR; AMINES; LIGAND;

D O I：

10.1016/j.tetlet.2008.09.159

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A continuous flow procedure has been elaborated for the copper(II)-mediated N- and O-arylation of a range of compounds with arylboronic acids using a commercial microreactor setup. The compounds could be continuously generated in good yields paving the way for efficient scalability. (C) 2008 Published by Elsevier Ltd.

引用

页码：15 / 18

页数：4

共 8 条

[1] New copper-mediated O-arylations of phenols with arylstannanes
Vakalopoulos, Alexandros
Kavazoudi, Xanthoula
Schoof, Joachim
[J]. TETRAHEDRON LETTERS, 2006, 47 (48) : 8607 - 8610
[2] New N- and O-arylations with phenylboronic acids and cupric acetate
Chan, DMT
Monaco, KL
Wang, RP
Winters, MP
[J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
[3] New N- and O-arylations with potassium aryltrifluoroborates and cupric acetate
Ajello, CW
Le Bourdonnec, B
Dolle, RE
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U130 - U130
[4] Base-mediated N- and O-arylations of NH-containing heterocycles, heterocyclic amines and phenols
Ghasemi, Zarrin
Shahrak, Nasim Shahi
Roomi, Behzad Jalali
Zakeri, Ziba
[J]. JOURNAL OF CHEMICAL RESEARCH, 2015, (02) : 73 - 75
[5] A general route for synthesis of N-aryl phenoxazines via copper(I)-catalyzed N-, N-, and O-arylations of 2-aminophenols
Liu, Nan
Wang, Bo
Chen, Wenwen
Liu, Chulong
Wang, Xinyan
Hu, Yuefei
[J]. RSC ADVANCES, 2014, 4 (93) : 51133 - 51139
[6] Ionic-liquid and cuprous sulfite containing halloysite nanoclay: An efficient catalyst for Click reaction as well as N- and O-arylations
Sadjadi, Samahe
Heravi, Majid M.
Malmir, Masoumeh
Kahangi, Fatemeh Ghoreyshi
[J]. APPLIED CLAY SCIENCE, 2018, 162 : 192 - 203
[7] The solid copper-mediated C-N cross-coupling of phenylboronic acids under continuous flow conditions
Bao, Jennifer
Tranmer, Geoffrey K.
[J]. TETRAHEDRON LETTERS, 2016, 57 (06) : 654 - 657
[8] N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with O-acetyl hydroxamic acids
Zhang, Zhihui
Yu, Ying
Liebeskind, Lanny S.
[J]. ORGANIC LETTERS, 2008, 10 (14) : 3005 - 3008

← 1 →