|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.
|Published in :||Chemistry - a European journal|
|Publisher / Ed. Institution :||Wiley|
|License (according to publishing contract) :||Licence according to publishing contract|
|Type of review:||Peer review (Publication)|
|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.|
|Departement:||Life Sciences and Facility Management|
|Publication type:||Article in scientific Journal|
|Appears in Collections:||Publikationen Life Sciences und Facility Management|
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