We describe a regioselective diborylation of primary benzylic C–H bonds catalyzed by [Ir(COD)OMe]2 and 4,4′-di-tert-butyl-2,2′-bipyridine (dtbpy). The hydrosilyl group acts as a traceless directing group, providing access to a range of 1,1-benzyldiboronate esters in good yields. Transformations of the 1,1-be
Yu-Chao Yuan, Christian Bruneau, Thierry Roisnel, Rafael Gramage-Doria, Site-selective Ru-catalyzed C–H bond alkenylation with biologically relevant isoindolinones: a case of catalyst performance controlled by subtle stereo-electronic effects of the weak directing group, Catalysis Science & Technology, 10.1039/C9CY01231A, (2019). A traceless directing group for C-H borylation. Dec 02, 2013 Publications - Glorius Research Group Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron-Donor-Acceptor Complex, -Catalyzed C–H Activation: Traceless Directing Group Enabled Regioselective Annulation, Angew. Chem. Int. Group 9 Transition Metal-Catalyzed C-H Halogenations, Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate
ChemInform Abstract: Iridium-Catalyzed Diborylation of
The protocol developed by Smith and Maleczka can be used as an example here, with the Bpin group serving as a traceless directing group for the selective C−H borylation of indoles into the 3 position . The indole S18-2 is smoothly converted into the N-borylated indole S18-3 by means of the reaction with HBpin. Jan 01, 2017 · In 2011, Larrosa and co-workers disclosed a method for formal meta-C H arylation using carboxylic acids as a traceless ortho-directing group (Scheme 8.43) with aryl iodides as coupling partners, which was compatible with a wide range of meta-substituents (Scheme 8.44). 84 Importantly, this tandem directed C H arylation/protodecarboxylation Undirected C-H Bond Activation of Arenes: [Rh(III)Cp*]-Catalyzed Dehydrogenative Alkene-Arene Coupling as New Pathway for the Selective Synthesis of Highly Substituted Z-Olefins, Chem. Asian J. 2012 , 7 , 1208-1212.
Apr 04, 2018 · Inner-sphere mechanism may be two types, for example, i) chelate-directed 14 ortho borylation, where a substrate having a directed metallation group coordinate to the metal of the 14-electron intermediate to create a 16-electron intermediate, which has an empty coordination site that can assist the cleavage of an ortho C H bond; and ii) a relay
directing group imine derivative stable metallacycle + less favorable de-insertion of an isocyanide 18.9. Functionalization of C-H Bonds by Carbene Insertions secondary C-H > tertially C-H > primary C-H bond energy steric factor favorable at sites that stabilize a buildup positive charge (favored: to O, N disfavored: to ester, OAc) aliphatic C Categories: C-H Bond Formation > Protodeboronations. Recent Literature. A mild gold-catalyzed protodeboronation reaction can be carried out in green solvents without any acid or base additives. Therefore, the reaction is very functional-group-tolerant and enables the use of the boronic acid group as an effective traceless directing or blocking