36043-87-5Relevant articles and documents
Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts
Davis, Holly J.,Mihai, Madalina T.,Phipps, Robert J.
supporting information, p. 12759 - 12762 (2016/10/13)
The use of noncovalent interactions to direct transition-metal catalysis is a potentially powerful yet relatively underexplored strategy, with most investigations thus far focusing on using hydrogen bonds as the controlling element. We have developed an ion pair-directed approach to controlling regioselectivity in the iridium-catalyzed borylation of two classes of aromatic quaternary ammonium salts, leading to versatile meta-borylated products. By examining a range of substituted substrates, this provides complex, functionalized aromatic scaffolds amenable to rapid diversification and more broadly demonstrates the viability of ion-pairing for control of regiochemistry in transition-metal catalysis.
Stereochemistry of Photosolvolysis of (-)-1-Phenylethyltrimethylammonium Iodide in Water and in Methanol, and Nucleophile Capture Ratios during Photosolvolysis of Some Benzylammonium Salts
Lillis, Veronica,Kenna, James Mc,Kenna, Jean Mc,Smith, Martin J.,Taylor, Paul S.,Williams, Ian H.
, p. 83 - 86 (2007/10/02)
The photosolvolysis of (-)-1-phenylethyltrimethylammonium iodide in water or methanol is characterised by extensive racemisation accompanied by some net configurational inversion, a result similar to that generally observed in thermal solvolysis via ion-pairs at chiral secondary centres.Recovered quaternary salt from the photolysis in water is only slightly if at all racemised, while likewise there is no observable epimerisation at nitrogen in recovered benzylammonium salts following photolysis in methanol of suitable derivatives of camphidine, trans-decahydroquinoline, and 4-phenylpiperidine.A strong preference for formation of the methyl ether rather than the alcohol is exhibited on either photochemical or thermal solvolysis of 1-p-methoxyphenylethyltrimethylammonium iodide in aqueous methanol, but nucleophile capture ratios during photosolvolysis of simple benzyltrimethylammonium salts in this mixed solvent system are much lower.
