Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium

2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,4-dioxane is essential for this CH bond activ...

Full description

Bibliographic Details
Main Authors: Ilies, Laurean, Kobayashi, Motoaki, Matsumoto, Arimasa, Yoshikai, Naohiko, Nakamura, Eiichi
Other Authors: School of Physical and Mathematical Sciences
Format: Journal Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/98283
http://hdl.handle.net/10220/12334
_version_ 1826113191240794112
author Ilies, Laurean
Kobayashi, Motoaki
Matsumoto, Arimasa
Yoshikai, Naohiko
Nakamura, Eiichi
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ilies, Laurean
Kobayashi, Motoaki
Matsumoto, Arimasa
Yoshikai, Naohiko
Nakamura, Eiichi
author_sort Ilies, Laurean
collection NTU
description 2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,4-dioxane is essential for this CH bond activation reaction. The reaction has wider scope of the substrate compared with the reaction using a separately prepared Grignard reagent, and proceeds with lower catalyst loading (2.5 mol%).
first_indexed 2024-10-01T03:19:09Z
format Journal Article
id ntu-10356/98283
institution Nanyang Technological University
language English
last_indexed 2024-10-01T03:19:09Z
publishDate 2013
record_format dspace
spelling ntu-10356/982832020-03-07T12:34:46Z Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium Ilies, Laurean Kobayashi, Motoaki Matsumoto, Arimasa Yoshikai, Naohiko Nakamura, Eiichi School of Physical and Mathematical Sciences 2-Arylpyridines, 2-alkenylpyridine, and aromatic imines can be coupled with aryl bromides in the presence of an iron catalyst, metallic magnesium, a diamine ligand and an organic dihalide oxidant at 0 °C. The use of a 1:1 mixture of tetrahydrofuran and 1,4-dioxane is essential for this CH bond activation reaction. The reaction has wider scope of the substrate compared with the reaction using a separately prepared Grignard reagent, and proceeds with lower catalyst loading (2.5 mol%). 2013-07-26T01:51:46Z 2019-12-06T19:53:09Z 2013-07-26T01:51:46Z 2019-12-06T19:53:09Z 2012 2012 Journal Article Ilies, L., Kobayashi, M., Matsumoto, A., Yoshikai, N., & Nakamura, E. (2012). Iron-Catalyzed Nitrogen-Directed Coupling of Arene and Aryl Bromides Mediated by Metallic Magnesium. Advanced Synthesis & Catalysis, 354(4), 593-596. 1615-4150 https://hdl.handle.net/10356/98283 http://hdl.handle.net/10220/12334 10.1002/adsc.201100791 en Advanced synthesis & catalysis © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
spellingShingle Ilies, Laurean
Kobayashi, Motoaki
Matsumoto, Arimasa
Yoshikai, Naohiko
Nakamura, Eiichi
Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title_full Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title_fullStr Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title_full_unstemmed Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title_short Iron-catalyzed nitrogen-directed coupling of arene and aryl bromides mediated by metallic magnesium
title_sort iron catalyzed nitrogen directed coupling of arene and aryl bromides mediated by metallic magnesium
url https://hdl.handle.net/10356/98283
http://hdl.handle.net/10220/12334
work_keys_str_mv AT ilieslaurean ironcatalyzednitrogendirectedcouplingofareneandarylbromidesmediatedbymetallicmagnesium
AT kobayashimotoaki ironcatalyzednitrogendirectedcouplingofareneandarylbromidesmediatedbymetallicmagnesium
AT matsumotoarimasa ironcatalyzednitrogendirectedcouplingofareneandarylbromidesmediatedbymetallicmagnesium
AT yoshikainaohiko ironcatalyzednitrogendirectedcouplingofareneandarylbromidesmediatedbymetallicmagnesium
AT nakamuraeiichi ironcatalyzednitrogendirectedcouplingofareneandarylbromidesmediatedbymetallicmagnesium