Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex
Non-activated alkyl halides are challenging substrates for cross-coupling reactions because they are reluctant to undergo oxidative addition and because metal alkyl intermediates are prone to ?-H elimination. Despite recent progress, well-defined catalysts are rare. We recently prepared Ni...
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2010-04-01
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| Series: | CHIMIA |
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| Online Access: | https://www.chimia.ch/chimia/article/view/4838 |
| _version_ | 1818281956848173056 |
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| author | Xile Hu |
| author_facet | Xile Hu |
| author_sort | Xile Hu |
| collection | DOAJ |
| description |
Non-activated alkyl halides are challenging substrates for cross-coupling reactions because they are reluctant to undergo oxidative addition and because metal alkyl intermediates are prone to ?-H elimination. Despite recent progress, well-defined catalysts are rare. We recently
prepared Ni complexes with a chelating pincer-type bis(amino)amide ligand. The chloride complex [(MeNN2)NiCl] is an active (pre)catalyst for the coupling of non-activated alkyl halides with alkyl, aryl, and heteroaryl Grignard reagents. The catalysis tolerates a wide
range of functional groups such as keto, ester, amide, acetal, indole, furan, nitrile, etc. The Ni complex also catalyzes direct alkylation of alkynes and aromatic heterocycles.
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| first_indexed | 2024-12-13T00:13:22Z |
| format | Article |
| id | doaj.art-f1f817d50bab409f939e6a4427c89ce0 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-13T00:13:22Z |
| publishDate | 2010-04-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-f1f817d50bab409f939e6a4427c89ce02022-12-22T00:05:53ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242010-04-0164410.2533/chimia.2010.231Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer ComplexXile Hu0Ecole Polytechnique Fédérale de Lausanne, Institute of Chemical Sciences and Engineering, EPFL-ISIC-LSCI, CH-1015 Lausanne;, Email: xile.hu@epfl.ch Non-activated alkyl halides are challenging substrates for cross-coupling reactions because they are reluctant to undergo oxidative addition and because metal alkyl intermediates are prone to ?-H elimination. Despite recent progress, well-defined catalysts are rare. We recently prepared Ni complexes with a chelating pincer-type bis(amino)amide ligand. The chloride complex [(MeNN2)NiCl] is an active (pre)catalyst for the coupling of non-activated alkyl halides with alkyl, aryl, and heteroaryl Grignard reagents. The catalysis tolerates a wide range of functional groups such as keto, ester, amide, acetal, indole, furan, nitrile, etc. The Ni complex also catalyzes direct alkylation of alkynes and aromatic heterocycles. https://www.chimia.ch/chimia/article/view/4838Alkyl halidesCross couplingC–h functionalizationGrignard reagentsNickel |
| spellingShingle | Xile Hu Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex CHIMIA Alkyl halides Cross coupling C–h functionalization Grignard reagents Nickel |
| title | Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex |
| title_full | Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex |
| title_fullStr | Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex |
| title_full_unstemmed | Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex |
| title_short | Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex |
| title_sort | cross coupling of non activated alkyl halides by a nickel pincer complex |
| topic | Alkyl halides Cross coupling C–h functionalization Grignard reagents Nickel |
| url | https://www.chimia.ch/chimia/article/view/4838 |
| work_keys_str_mv | AT xilehu crosscouplingofnonactivatedalkylhalidesbyanickelpincercomplex |