A5000048334- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Asymmetric Hydrogenation and Catalysis
- X-ray Diffraction in Crystallography
- Organoboron and organosilicon chemistry
- Crystallization and Solubility Studies
University of California, Berkeley
2018-2024
A rhodium-catalyzed intramolecular silylation of alkyl C-H bonds has been developed that occurs with unusual selectivity for the located δ to oxygen atom an alcohol-derived silyl ether over typically more reactive proximal same atom. (Hydrido)silyl ethers, generated in situ by dehydrogenative coupling tertiary alcohols diethylsilane, undergo regioselective at a primary bond hydroxyl group presence [(Xantphos)Rh(Cl)] as catalyst. Oxidation resulting 6-membered oxasilolanes generates...
We report a new system for the silylation of aryl C–H bonds. The combination [Ir(cod)(OMe)]2 and 2,9-Me2-phenanthroline (2,9-Me2-phen) catalyzes arenes at lower temperatures with faster rates than those reported previously, when hydrogen byproduct is removed, high functional group tolerance regioselectivity. Inhibition reactions by H2 shown to limit bonds in presence most active catalysts, thereby masking their activity. Analysis initial uncovered reactivity catalyst containing sterically...
The steric effects of substituents on five-membered rings are less pronounced than those six-membered because the difference in bond angles. Thus, regioselectivities reactions heteroarenes that occur with selectivities dictated by effects, such as borylation C-H bonds, have been poor many cases. We report silylation five-membered-ring occurs high sterically derived regioselectivity when catalyzed combination [Ir(cod)(OMe)]
Phenanthroline ligands and [Ir(cod)(OMe)]2 form complexes that catalyze the silylation of aromatic aliphatic C–H bonds. However, no experimental data on identity related to mechanism this process or mechanisms by which they react functionalize bonds have been reported. Herein, we describe our studies iridium-catalyzed aryl The resting state catalyst is an iridium disilyl hydride complex (phenanthroline)Ir(SiMe(OTMS)2)2(H)(L), in L varies with arene additives. An was isolated, characterized,...
The steric effects of substituents on five-membered rings are less pronounced than those six-membered because the difference in bond angles. Thus, regioselectivities reactions that occur with selectivities dictated by effects, such as borylation C-H bonds, have been poor many cases. We report silylation ring heteroarenes occurs high sterically derived regioselectivity when catalyzed combination [Ir(cod)(OMe)]
The functionalization of C-H bonds enables the modification complex molecules, often with intention forming compound libraries. borylation aryl is a widely used class bond functionalization, and conventional catalyst systems for consist an iridium source
We report that the silylation of five-membered ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by combination of[Ir(cod)(OMe)]2 and a phenanthroline ligand or new pyridylimidazoline further increases regioselectivity. The reactions these catalysts produce yields heteroarylsilanes from functionalization at most accessible C–H bonds rings under conditions borylation previously reported formed mixtures products are unstable.
We report a new system for the silylation of aryl C-H bonds. The combination [Ir(cod)(OMe)] 2 and 2,9-Me -phenanthroline (2,9-Me phen) catalyzes arenes at lower temperatures with faster rates than those reported previously, when hydrogen byproduct is removed, high functional group tolerance regioselectivity. Inhibition reactions by H shown to limit bonds in presence most active catalysts, thereby masking their activity. Analysis initial uncovered reactivity catalyst containing sterically...
<div>We report that the silylation of five-membered ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by combination of</div><div>[Ir(cod)(OMe)]2 and a phenanthroline ligand or new pyridylimidazoline further increases regioselectivity. The reactions these catalysts produce yields heteroarylsilanes from functionalization at most accessible C–H bonds rings under conditions borylation previously reported formed mixtures products are...
We report a new system for the silylation of aryl C-H bonds. The combination [Ir(cod)(OMe)]<sub>2</sub> and 2,9-Me<sub>2</sub>-phenanthroline (2,9-Me<sub>2</sub>phen) catalyzes arenes at lower temperatures with faster rates than those reported previously, when hydrogen byproduct is removed, high functional group tolerance regioselectivity. Inhibition reactions by H<sub>2</sub> shown to limit bonds in presence most active catalysts, thereby...
<p>The iridium-catalyzed silylation of aromatic C–H bonds has become a synthetically valuable reaction because it forms aryl silanes with high sterically derived regioselectivity silane reagents that are produced and consumed on large scales. Many groups, including our own, have reported iridium complexes phenanthroline or bipyridine ligands as catalysts for this reaction. Yet, little is known about the mechanism by which arenes occurs. Indeed, no iridium-silyl been prepared react C-H...
The iridium-catalyzed silylation of aromatic C–H bonds has become a synthetically valuable reaction because it forms aryl silanes with high sterically derived regioselectivity silane reagents that are produced and consumed on large scales. Many groups, including our own, have reported iridium complexes phenanthroline or bipyridine ligands as catalysts for this reaction. Yet, little is known about the mechanism by which arenes occurs. Indeed, no iridium-silyl been prepared react C-H to form...