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

Abstract

The reaction mechanisms of the platinum-catalyzed domino reaction to access C5- or C6-alkynylated indoles have been theoretically investigated by employing the density functional theory (DFT) calculations. Our calculation results are agreement with the experimental facts that the C5- and C6-alkynylated indoles are the major products by using the C2- and C3-substituted pyrrole as the corresponding substrates, respectively. Based on our mechanistic study, the additive HCO3- used in the experiment are proved 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-controlling regioselectivity is dominated by the electronic effects.

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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, Accepted Manuscript
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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, Accepted Manuscript , DOI: 10.1039/C7NJ03063K

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