81852-70-2Relevant academic research and scientific papers
Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules
La Manna, Pellegrino,Talotta, Carmen,Floresta, Giuseppe,De Rosa, Margherita,Soriente, Annunziata,Rescifina, Antonio,Gaeta, Carmine,Neri, Placido
, p. 5423 - 5428 (2018/04/09)
A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.
Gold(I)-Catalysed Hydroarylation of 1,3-Disubstituted Allenes with Efficient Axial-to-Point Chirality Transfer
Sutherland, Daniel R.,Kinsman, Luke,Angiolini, Stuart M.,Rosair, Georgina M.,Lee, Ai-Lan
supporting information, p. 7002 - 7009 (2018/04/30)
Hydroarylation of enantioenriched 1,3-disubstituted allenes has the potential to proceed with axial-to-point chirality transfer to yield enantioenriched allylated (hetero)aryl compounds. However, the gold-catalysed intermolecular reaction was previously reported to occur with no chirality transfer owing to competing allene racemisation. Herein, we describe the development of the first intermolecular hydroarylations of allenes to proceed with efficient chirality transfer and summarise some of the key criteria for achieving high regio- and stereoselectivity.
Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction
Stoner, Eric J.,Cothron, Darlene A.,Balmer, Mary K.,Roden, Brian A.
, p. 11043 - 11062 (2007/10/02)
A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.
