Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation

Naohiko Yoshikai; Hiroko Mashima; Eiichi Nakamura

doi:10.1021/ja056327n

Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation

Naohiko Yoshikai, Hiroko Mashima, Eiichi Nakamura

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

103 Citations (Scopus)

Abstract

Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf _≫ ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.

Original language	English
Pages (from-to)	17978-17979
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	51
DOIs	https://doi.org/10.1021/ja056327n
Publication status	Published - 2005 Dec 28
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf ≫ ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.",

author = "Naohiko Yoshikai and Hiroko Mashima and Eiichi Nakamura",

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T1 - Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation

AU - Yoshikai, Naohiko

AU - Mashima, Hiroko

AU - Nakamura, Eiichi

PY - 2005/12/28

Y1 - 2005/12/28

N2 - Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf ≫ ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.

AB - Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf ≫ ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.

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Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation

Abstract

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