| 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 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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