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Issue 22, 2017
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The regioselectivity in the platinum-catalyzed domino reaction to access alkynylated indoles: a theoretical study

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Abstract

The reaction mechanisms of the platinum-catalyzed domino reaction to access C5- or C6-alkynylated indoles have been theoretically investigated by employing density functional theory (DFT) calculations. Our calculation results are in agreement with the experimental facts that C5- and C6-alkynylated indoles are the major products obtained by using C2- and C3-substituted pyrroles as the corresponding substrates, respectively. Based on our mechanistic study, the HCO3 additive used in the experiment is proven to play an important role in promoting deprotonation and aromatization steps. Through investigating the natural bond orbital (NBO) charges of the regioselectivity-determining transition states, one can find that the substrate-controlled regioselectivity is dominated by the electronic effects.

Graphical abstract: The regioselectivity in the platinum-catalyzed domino reaction to access alkynylated indoles: a theoretical study

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Publication details

The article was received on 17 Aug 2017, accepted on 05 Oct 2017 and first published on 05 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ03063K
Citation: New J. Chem., 2017,41, 13798-13803
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    The regioselectivity in the platinum-catalyzed domino reaction to access alkynylated indoles: a theoretical study

    L. Han, L. Nie and T. Liu, New J. Chem., 2017, 41, 13798
    DOI: 10.1039/C7NJ03063K

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