[Cp∗IrCl2]2-catalysed cyclization of 2-alkynylanilines into indoles
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Acknowledgments
This work was supported by Nanyang Technological University and the Ministry of Education (Research Grant No. M4011017). One of us (E.K.) thanks the Nanyang Technological University for a Research Scholarship.
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2018, Journal of Organometallic ChemistryCitation Excerpt :In accordance with the experimental conditions, pyridine and toluene solvents were employed for reactions involving alkynyl amine and amide respectively. It is known that DFT calculations could overestimate the entropic effect [25]. The translational entropy correction in solution was incorporated using the method proposed by Whitesides et al. [26] Unless specified otherwise, the solvation Gibbs free energy was used for discussion and it was obtained from the addition of the solvation single-point energy and the thermal correction to the Gibbs free energy.
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2015, Progress in Heterocyclic ChemistryCitation Excerpt :This is reported to be the first example of a combined catalytic indole generation and subsequent enantioselective addition of carbonyl compounds (14CS1585). Other indole syntheses of this type include a [Cp∗IrCl2]2-catalyzed cyclization of 2-alkynylanilines (14TL5495), a dearomatization/metal-catalyzed domino reaction of 2-alkynylanilines to give azepino[5,4,3-cd]indoles (14OL816) or 4-acetonylindoles (14OL3600), triazoloindoles as α-imino rhodium carbene precursors (14OL1244), and the silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines (14CC3024). As an orthogonal approach to the direct trifluoromethylation of indole derivatives, 2-trifluoromethylated indole 93 was prepared by subjecting isonitrile 92 to the hypervalent iodide (Togni) reagent and catalytic amounts of tetrabutylammonium iodide.