Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls

Gerber, Roman; Frech, Christian M.

doi:10.1002/chem.201101037

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls
Authors:	Gerber, Roman Frech, Christian M.
DOI:	10.1002/chem.201101037
Published in:	Chemistry - A European Journal
Volume(Issue):	17
Issue:	42
Page(s):	11893
Pages to:	11904
Issue Date:	2011
Publisher / Ed. Institution:	Wiley
ISSN:	0947-6539 1521-3765
Language:	English
Subject (DDC):	540: Chemistry
Abstract:	Treatment of NMP solutions of NiCl(2) with 1,1',1''-(phosphanetriyl)tripiperidine (≈2.05 equiv), dissolved in THF, in air at 25°C forms a highly active catalytic system for the cross-coupling of a large variety of electronically activated, non-activated, deactivated, and ortho-substituted, heterocyclic, and functionalized aryl bromides and aryl chlorides with diarylzinc reagents. Very high levels of conversion and yields were obtained within 2 h at 60°C in the presence of only 0.1 mol% of catalyst (based on nickel) and thus at catalyst loadings far lower than typically reported for nickel-catalyzed versions of the Negishi reaction. Various aryl halides-which may contain trifluoromethyl groups, fluorides, or other functional groups such as acetals, ketones, ethers, esters, lactones, amides, imines, anilines, alkenes, pyridines, quinolines, and pyrimidines-were successfully converted into the corresponding biaryls. Electronic and steric variations are tolerated in both reaction partners. Experimental observations indicate that a molecular (Ni(I)/Ni(III)) mechanism is operative.
URI:	https://digitalcollection.zhaw.ch/handle/11475/9850
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Appears in collections:	Publikationen Life Sciences und Facility Management

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Gerber, R., & Frech, C. M. (2011). Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls. Chemistry - A European Journal, 17(42), 11893–11904. https://doi.org/10.1002/chem.201101037

Gerber, R. and Frech, C.M. (2011) ‘Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls’, Chemistry - A European Journal, 17(42), pp. 11893–11904. Available at: https://doi.org/10.1002/chem.201101037.

R. Gerber and C. M. Frech, “Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls,” Chemistry - A European Journal, vol. 17, no. 42, pp. 11893–11904, 2011, doi: 10.1002/chem.201101037.

GERBER, Roman und Christian M. FRECH, 2011. Negishi cross-coupling reactions catalyzed by an aminophosphine-based nickel system : a reliable and general applicable reaction protocol for the high-yielding synthesis of biaryls. Chemistry - A European Journal. 2011. Bd. 17, Nr. 42, S. 11893–11904. DOI 10.1002/chem.201101037

Gerber, Roman, and Christian M. Frech. 2011. “Negishi Cross-Coupling Reactions Catalyzed by an Aminophosphine-Based Nickel System : A Reliable and General Applicable Reaction Protocol for the High-Yielding Synthesis of Biaryls.” Chemistry - A European Journal 17 (42): 11893–904. https://doi.org/10.1002/chem.201101037.

Gerber, Roman, and Christian M. Frech. “Negishi Cross-Coupling Reactions Catalyzed by an Aminophosphine-Based Nickel System : A Reliable and General Applicable Reaction Protocol for the High-Yielding Synthesis of Biaryls.” Chemistry - A European Journal, vol. 17, no. 42, 2011, pp. 11893–904, https://doi.org/10.1002/chem.201101037.