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Iridium Catalyzed Enantioselective Intermolecular Indole C2-Allylation

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JournalAngewandte Chemie International Edition
DateAccepted/In press - 21 Feb 2020
DateE-pub ahead of print - 24 Feb 2020
DatePublished (current) - 4 May 2020
Issue number19
Pages (from-to)7598-7604
Early online date24/02/20
Original languageEnglish


The enantioselective intermolecular C2-allylation of 3-substituted indoles is reported for the first time. This directing group-free approach relies on a chiral Ir-(P, olefin) complex and Mg(ClO4)2 Lewis acid catalyst system to promote allylic substitution, providing the C2-allylated products in typically high yields (40-99%) and enantioselectivities (83-99% ee) with excellent regiocontrol. Experimental studies and DFT calculations suggest that the reaction proceeds via direct C2-allylation, rather than C3-allylation followed by in situ migration. Steric congestion at the indole-C3 position and improved π-π stacking interactions have been identified as major contributors to the C2-selectivity.

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