Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand

Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand

A new diphosphine (POP) ligand bearing an alkoxide group allows us to synthesize partially fluorinated arenes. A nickel-catalyzed cross-coupling between a polyfluoroarene and an organozinc reagent in the presence of POP selectively produces a monosubstitution product. Aryl and alkylzinc reagents smo...

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Main Authors: Nakamura, Yuki, Yoshikai, Naohiko, Ilies, Laurean, Nakamura, Eiichi
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/97397
http://hdl.handle.net/10220/10609
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-973972020-03-07T12:34:43Z Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand Nakamura, Yuki Yoshikai, Naohiko Ilies, Laurean Nakamura, Eiichi School of Physical and Mathematical Sciences A new diphosphine (POP) ligand bearing an alkoxide group allows us to synthesize partially fluorinated arenes. A nickel-catalyzed cross-coupling between a polyfluoroarene and an organozinc reagent in the presence of POP selectively produces a monosubstitution product. Aryl and alkylzinc reagents smoothly take part in the reaction. It is speculated that monosubstitution is the result of accelerated product expulsion from the product/catalyst complex. 2013-06-25T04:05:28Z 2019-12-06T19:42:12Z 2013-06-25T04:05:28Z 2019-12-06T19:42:12Z 2012 2012 Journal Article Nakamura, Y., Yoshikai, N., Ilies, L., & Nakamura, E. (2012). Nickel-Catalyzed Monosubstitution of Polyfluoroarenes with Organozinc Reagents Using Alkoxydiphosphine Ligand. Organic Letters, 14(13), 3316-3319. 1523-7060 https://hdl.handle.net/10356/97397 http://hdl.handle.net/10220/10609 10.1021/ol301195x en Organic letters © 2012 American Chemical Society.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
description A new diphosphine (POP) ligand bearing an alkoxide group allows us to synthesize partially fluorinated arenes. A nickel-catalyzed cross-coupling between a polyfluoroarene and an organozinc reagent in the presence of POP selectively produces a monosubstitution product. Aryl and alkylzinc reagents smoothly take part in the reaction. It is speculated that monosubstitution is the result of accelerated product expulsion from the product/catalyst complex.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Nakamura, Yuki
Yoshikai, Naohiko
Ilies, Laurean
Nakamura, Eiichi
format Article
author Nakamura, Yuki
Yoshikai, Naohiko
Ilies, Laurean
Nakamura, Eiichi
spellingShingle Nakamura, Yuki
Yoshikai, Naohiko
Ilies, Laurean
Nakamura, Eiichi
Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
author_sort Nakamura, Yuki
title Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
title_short Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
title_full Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
title_fullStr Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
title_full_unstemmed Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
title_sort nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand
publishDate 2013
url https://hdl.handle.net/10356/97397
http://hdl.handle.net/10220/10609
_version_ 1681043291926167552

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