A General Strategy for the Nickel-Catalyzed C−H Alkylation of Anilines
The C−H alkylation of aniline derivatives with both primary and secondary alkyl halides was achieved with a versatile nickel catalyst of a vicinal diamine ligand. Step‐economic access to functionalized 2‐pyrimidyl anilines, key structural motifs in anticancer drugs, is thus provided. The C−H functio...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-02, Vol.55 (9), p.3153-3157 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Ruan, Zhixiong Lackner, Sebastian Ackermann, Lutz |
| description | The C−H alkylation of aniline derivatives with both primary and secondary alkyl halides was achieved with a versatile nickel catalyst of a vicinal diamine ligand. Step‐economic access to functionalized 2‐pyrimidyl anilines, key structural motifs in anticancer drugs, is thus provided. The C−H functionalization proceeded through facile C−H activation and SET‐type C−X bond cleavage with the assistance of a monodentate directing group, which could be removed in a traceless fashion.
One for all: An inexpensive nickel catalyst enables the C−H alkylation of pyrimidyl anilines with both primary and secondary alkyl halides. The directing group (DG) could be easily removed in a traceless fashion, and the products contain key structural motifs of important anticancer drugs. |
| doi_str_mv | 10.1002/anie.201510743 |
| format | Article |
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| language | eng |
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| subjects | Alkylation Aniline anilines Antineoplastic drugs Antitumor agents Catalysts C−H activation Drugs Halides Nickel reaction mechanisms |
| title | A General Strategy for the Nickel-Catalyzed C−H Alkylation of Anilines |
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