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

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DC Field	Value	Language
dc.contributor.author	Gerber, Roman	-
dc.contributor.author	Frech, Christian M.	-
dc.date.accessioned	2018-08-28T14:46:49Z	-
dc.date.available	2018-08-28T14:46:49Z	-
dc.date.issued	2011	-
dc.identifier.issn	0947-6539	de_CH
dc.identifier.issn	1521-3765	de_CH
dc.identifier.uri	https://digitalcollection.zhaw.ch/handle/11475/9850	-
dc.description.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.	de_CH
dc.language.iso	en	de_CH
dc.publisher	Wiley	de_CH
dc.relation.ispartof	Chemistry - A European Journal	de_CH
dc.rights	Licence according to publishing contract	de_CH
dc.subject.ddc	540: Chemie	de_CH
dc.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	de_CH
dc.type	Beitrag in wissenschaftlicher Zeitschrift	de_CH
dcterms.type	Text	de_CH
zhaw.departement	Life Sciences und Facility Management	de_CH
dc.identifier.doi	10.1002/chem.201101037	de_CH
dc.identifier.pmid	21887715	de_CH
zhaw.funding.eu	No	de_CH
zhaw.issue	42	de_CH
zhaw.originated.zhaw	No	de_CH
zhaw.pages.end	11904	de_CH
zhaw.pages.start	11893	de_CH
zhaw.publication.status	publishedVersion	de_CH
zhaw.volume	17	de_CH
zhaw.publication.review	Peer review (Publikation)	de_CH
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.