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Issue 22, 2018
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Ni-Catalyzed dehydrogenative coupling of primary and secondary alcohols with methyl-N-heteroaromatics

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Abstract

Here we report the first base-metal catalyzed dehydrogenative coupling of primary (aromatic, heteroaromatic, and aliphatic) and secondary alcohols with methyl-N-heteroaromatics to form various C(sp3)-alkylated N-heteroaromatics. The reaction is enabled by Earth abundant, non-precious NiBr2 as a transition metal catalyst and N,N,N′,N′-tetramethylethylenediamine (TMEDA) as a ligand system. Mechanistic studies reveal that a hydrogen auto-transfer process is involved in the direct C(sp3)-alkylation and the reaction proceeds through an α-olefination process.

Graphical abstract: Ni-Catalyzed dehydrogenative coupling of primary and secondary alcohols with methyl-N-heteroaromatics

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Publication details

The article was received on 25 Jul 2018, accepted on 26 Sep 2018 and first published on 26 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00764K
Citation: Org. Chem. Front., 2018,5, 3250-3255
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    Ni-Catalyzed dehydrogenative coupling of primary and secondary alcohols with methyl-N-heteroaromatics

    J. Rana, R. Babu, M. Subaramanian and E. Balaraman, Org. Chem. Front., 2018, 5, 3250
    DOI: 10.1039/C8QO00764K

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