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Nickel-Catalyzed Stereospecific C-H Coupling of Benzamides with Epoxides.
Angew Chem Int Ed Engl
September 2018
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
A Ni(OAc) -catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with epoxides has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to form the corresponding 3,4-dihydroisocoumarins directly. Additionally, the nickel catalysis is stereospecific, and the cis- and trans-epoxides are converted into the corresponding cis- and trans-dihydroisocoumarins with retention of configuration, which is complementary to previously reported palladium catalysis.
View Article and Find Full Text PDFCatalytic Asymmetric Csp3 -H Functionalization under Photoredox Conditions by Radical Translocation and Stereocontrolled Alkene Addition.
Angew Chem Int Ed Engl
October 2016
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043, Marburg, Germany.
This work demonstrates how photoredox-mediated C(sp )-H activation through radical translocation can be combined with asymmetric catalysis. Upon irradiation with visible light, α,β-unsaturated N-acylpyrazoles react with N-alkoxyphthalimides in the presence of a rhodium-based chiral Lewis acid catalyst and the photosensitizer fac-[Ir(ppy) ] to provide a C-C bond-formation product with high enantioselectivity (up to 97 % ee) and, where applicable, with some diastereoselectivity (3.0:1 d.
View Article and Find Full Text PDFNickel-catalyzed selective oxidative radical cross-coupling: an effective strategy for inert Csp3-H functionalization.
Org Lett
February 2015
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, PR China.
An effective strategy for inert Csp(3)-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp(3)-H arylation products in good yields.
View Article and Find Full Text PDFMetal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism.
Nature
July 2013
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge.
View Article and Find Full Text PDFFunctionalization of Csp3-H and Csp2-H bonds: synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds.
Angew Chem Int Ed Engl
November 2012
EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK.
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