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Nickel-catalyzed C–H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(i)/Ni(iii) pathway

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Abstract

A mild and efficient nickel-catalyzed method for the coupling of unactivated primary and secondary alkyl chlorides with the C–H bond of indoles and pyrroles is described which demonstrates a high level of chemo and regioselectivity. The reaction tolerates numerous functionalities, such as halide, alkenyl, alkynyl, ether, thioether, furanyl, pyrrolyl, indolyl and carbazolyl groups including acyclic and cyclic alkyls under the reaction conditions. Mechanistic investigation highlights that the alkylation proceeds through a single-electron transfer (SET) process with Ni(I)-species being the active catalyst. Overall, the alkylation follows a Ni(I)/Ni(III) pathway involving the rate-influencing two-step single-electron oxidative addition of alkyl chlorides.

Graphical abstract: Nickel-catalyzed C–H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(i)/Ni(iii) pathway

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Publication details

The article was received on 24 Mar 2019, accepted on 17 Aug 2019 and first published on 19 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC01446B
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Nickel-catalyzed C–H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(I)/Ni(III) pathway

    D. K. Pandey, S. B. Ankade, A. Ali, C. P. Vinod and B. Punji, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC01446B

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