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

Yuki Nakamura; Naohiko Yoshikai; Laurean Ilies; Eiichi Nakamura

doi:10.1021/ol301195x

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

Yuki Nakamura, Naohiko Yoshikai, Laurean Ilies, Eiichi Nakamura

Research output: Contribution to journal › Article › peer-review

100 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3316-3319
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	13
DOIs	https://doi.org/10.1021/ol301195x
Publication status	Published - 2012 Jul 6
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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.",

author = "Yuki Nakamura and Naohiko Yoshikai and Laurean Ilies and Eiichi Nakamura",

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T1 - Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand

AU - Nakamura, Yuki

AU - Yoshikai, Naohiko

AU - Ilies, Laurean

AU - Nakamura, Eiichi

PY - 2012/7/6

Y1 - 2012/7/6

N2 - 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.

AB - 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.

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ER -

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

Abstract

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