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
Pages: 11893
Pages to: 11904
Issue Date: 2011
Publisher / Ed. Institution: Wiley
ISSN: 0947-6539
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.
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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