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Superelectrophilic Csp-H bond fluorination of aliphatic amines in superacid: the striking role of ammonium-carbenium dications.
Chem Commun (Camb)
June 2020
Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers, CNRS, Superacid Group in Organic Synthesis Team, F-86073 Poitiers, France.
The superacid-promoted electrophilic Csp3-H bond activation of aliphatic amines generates superelectrophilic species that can be subsequently fluorinated. Demonstrated by low-temperature in situ NMR experiments, the ammonium-carbenium dications, crucial for this reaction, can also react with C-H bonds opening future synthesis perspectives for this mode of activation.
View Article and Find Full Text PDFGold(i)-catalysed high-yielding synthesis of indenes by direct C-H bond activation.
Org Biomol Chem
October 2018
Universidad de Guanajuato, Departamento de Química, División de Ciencias Naturales y Exactas, Campus Guanajuato. Cerro de la Venada S/N, 36040, Guanajuato, Gto., Mexico.
A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp3-H activation under gold(i) catalysis was developed. The scope of the protocol was determined by synthesizing some electron-neutral, electron-poor as well as electron-rich derivatives including the dibenzofurane and carbazole heterocycles. The mechanism of this reaction was elucidated by theoretical calculations using a ONIOM(M08-HX/mixed-basis:PM6) hybrid scheme.
View Article and Find Full Text PDFSynthesis of a (N,C,C) Au(iii) pincer complex via C-H bond activation: increasing catalyst robustness by rational catalyst design.
Chem Commun (Camb)
October 2018
Department of Chemistry, University of Oslo, P. O. Box 1033 Blindern, N-0315 Oslo, Norway.
A (N,CAr,CAlk) Au(iii) pincer complex has been synthesized from Au(OAc)3 (OAc = OCOCH3) and 2-(3,5-di-tert-butylphenyl)pyridine (L1) involving a Csp3-H bond activation by electrophilic substitution. In agreement with DFT calculations, the resulting complex significantly improves the performance of Au(tpy)(OAcF)2 (tpy = 2-(p-tolyl)pyridine, OAcF = OCOCF3) in the catalytic trifluoroacetylation of acetylene.
View Article and Find Full Text PDFLigand-Enabled Enantioselective Csp3 -H Activation of Tetrahydroquinolines and Saturated Aza-Heterocycles by Rh.
Angew Chem Int Ed Engl
July 2018
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
The first rhodium(I)-catalyzed enantioselective intermolecular Csp3 -H activation of various saturated aza-heterocycles including tetrahydroquinolines, piperidines, piperazines, azetidines, pyrrolidines, and azepanes is presented. The combination of a rhodium(I) precatalyst and a chiral monodentate phosphonite ligand is shown to be a powerful catalytic system to access a variety of important enantio-enriched heterocycles from simple starting materials. Notably, the Csp3 -H activation of tetrahydroquinolines is especially challenging due to the adjacent Csp2 -H bond.
View Article and Find Full Text PDFCooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3 -H Bonds.
Angew Chem Int Ed Engl
June 2017
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
An unprecedented method that makes use of the cooperative interplay between molecular iodine and photoredox catalysis has been developed for dual light-activated intramolecular benzylic C-H amination. Iodine serves as the catalyst for the formation of a new C-N bond by activating a remote Csp3 -H bond (1,5-HAT process) under visible-light irradiation while the organic photoredox catalyst TPT effects the reoxidation of the molecular iodine catalyst. To explain the compatibility of the two involved photochemical steps, the key N-I bond activation was elucidated by computational methods.
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