86767-25-1Relevant articles and documents
Hydroarylation of Alkenes by Protonation/Friedel-Crafts Trapping: HFIP-Mediated Access to Per-aryl Quaternary Stereocenters
Nielsen, Christian D.-T.,White, Andrew J. P.,Sale, David,Bures, Jordi,Spivey, Alan C.
, p. 14965 - 14973 (2019/11/13)
Upon treatment with a combination of HFIP and an organic sulfonic acid, alkenes behave as Br?nsted bases and protonate to give carbocations which can be trapped by electron-rich arenes. The reaction constitutes a Friedel-Crafts hydroarylation which procee
Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones
Fernández-Mateos, Emilio,Maciá, Beatriz,Yus, Miguel
, p. 6519 - 6526 (2016/02/18)
We report a catalytic system for the challenging enantioselective addition of aryl Grignard reagents to ketones. Using a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities. The catalytic enantioselective addition of aryl Grignard reagents to ketones is now possible. Using a readily available Ar-BINMOL ligand and titanium(IV) isopropoxide in a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities.
Site-isolation and recycling of PdCl2 using PDMS thimbles
Miller II, A. Lee,Bowden, Ned B.
experimental part, p. 4834 - 4840 (2009/10/02)
(Chemical Equation Presented) Macroscopic thimbles composed of polydimethylsiloxane (PDMS) were used to site-isolate PdCl2 from the products of Wacker-Tsuji oxidations and Pd-mediated homocouplings. The reactions were completed on the interior of hollow thimbles, and the organic products were isolated by their selective flux to the exterior of the thimbles. Although organic molecules had high flux through the walls of the thimbles, PdCl 2 remained encapsulated as a result of its polar structure that rendered it insoluble in PDMS. In two examples, less than 0.002% of the PdCl2 added to the interior of the thimble partitioned to the exterior; thus, over 99.998% remained encapsulated on the interior of the thimble. Because it was encapsulated, this catalyst was readily recycled five times for the Wacker-Tsuji oxidation of styrene. A sequential reaction was also completed where p-methylstyrene was oxidized to 4′-methyl-acetophenone by PdCl2 on the interior of a thimble and then fluxed to the exterior to react with phenylmagnesium bromide to yield 1-phenyl-1-p-tolyl-ethanol. This method site-isolated PdCl2 catalysts without requiring them to be rendered heterogeneous, the addition of exogenous ligands, or any modifications to the catalyst. The catalyst was site-isolated by affecting its environment rather than by altering its ligand structure.
