Intermolecular aminoarylation of alkynes is described, addition of diarylanilines to alkynes and Smiles-Truce rearrangement. The transformation manipulates the C-N bond of anilines directly, with no requirement for organometallic reagents or transition metal catalysis. The enaminoate products are versatile building blocks for different classes of heterocycles.
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Aminoarylation of alkynes using diarylanilines.
Chem Commun (Camb)
June 2024
Dept of Chemistry, University of Manchester, Oxford Rd, Manchester M13 9PL, UK.
Intermolecular aminoarylation of alkynes is described, addition of diarylanilines to alkynes and Smiles-Truce rearrangement. The transformation manipulates the C-N bond of anilines directly, with no requirement for organometallic reagents or transition metal catalysis. The enaminoate products are versatile building blocks for different classes of heterocycles.
View Article and Find Full Text PDFCatalytic Alkyne Arylation Using Traceless Directing Groups.
Angew Chem Int Ed Engl
October 2018
Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, California, 92697, USA.
By using Pd /Mandyphos, we achieved a three-component aminoarylation of alkynes to generate enamines, which are then hydrolyzed to either α-arylphenones or α,α-diarylketones. This Pd-catalyzed method overcomes established known pathways to enable the use of amines as traceless directing groups for C-C bond formation.
View Article and Find Full Text PDFConstruction of Condensed Polycyclic Aromatic Frameworks through Intramolecular Cycloaddition Reactions Involving Arynes Bearing an Internal Alkyne Moiety.
Chemistry
November 2017
Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo, 101-0062, Japan.
Facile synthetic methods for condensed polycyclic aromatic compounds via aryne intermediates are reported. The generation of arynes bearing a (3-arylpropargyl)oxy group from the corresponding o-iodoaryl triflate-type precursors efficiently afforded arene-fused oxaacenaphthene derivatives, which were formed through intramolecular [2+4] cycloaddition. Extending the method to the generation of arynes bearing a 1,3-diyne moiety led to a continuous generation of naphthalyne intermediate through the hexadehydro Diels-Alder reaction involving the aryne triple bond.
View Article and Find Full Text PDFMetal-Free Intermolecular Aminoarylation of Alkynes.
Angew Chem Int Ed Engl
April 2017
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
A metal-free aminoarylation of internal alkynes is described, yielding tetrasubstituted enaminoates. The transformation proceeds in good to excellent yields through a tandem conjugate addition/Smiles rearrangement involving aryl and heteroaryl sulfonamides. Substrate scope is very broad under simple, user-friendly conditions, and the reaction can be used to easily access biologically active phenethylamine derivatives.
View Article and Find Full Text PDFCascade photoredox/gold catalysis: access to multisubstituted indoles via aminoarylation of alkynes.
Chem Commun (Camb)
December 2016
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China. and Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
A new method for the synthesis of 3-arylindoles has been developed by visible light mediated dual gold/photoredox catalysis. This transformation has many features such as cascade catalysis, high efficiency, redox-neutral reaction conditions and good functional group tolerance. The reaction proceeds through the photoredox-promoted formation of an electrophilic arylgold(iii) intermediate that undergoes coupling with the arylamine nucleophile.
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