847355-79-7Relevant academic research and scientific papers
Highly efficient and enantioselective α-arylation of cycloalkanones by scandium-catalyzed diazoalkane-carbonyl homologation
Rendina, Victor L.,Kaplan, Hilan Z.,Kingsbury, Jason S.
experimental part, p. 686 - 693 (2012/04/04)
Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo-alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo-methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation. Georg Thieme Verlag Stuttgart · New York.
Catalytic and regioselective ring expansion of arylcyclobutanones with trimethylsilyldiazomethane. Ligand-dependent entry to β-ketosilane or enolsilane adducts
Dabrowski, Jennifer A.,Moebius, David C.,Wommack, Andrew J.,Kornahrens, Anne F.,Kingsbury, Jason S.
supporting information; experimental part, p. 3598 - 3601 (2010/11/04)
Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)3 as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)3 g
Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes
Willis, Michael C.,Taylor, Dawn,Gillmore, Adam T.
, p. 11513 - 11520 (2007/10/03)
Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd2(dba)3 and the ligand DPEphos effects the key bond
Palladium-catalyzed tandem alkenyl and aryl C-N bond formation: A cascade N-annulation route to 1-functionalized indoles
Willis, Michael C.,Brace, Gareth N.,Holmes, Ian P.
, p. 403 - 406 (2007/10/03)
(Chemical Equation Presented) A single tandem operation allows rapid access to a variety of substituted N-functionalized indoles. The nitrogen atom of the indole nucleus is incorporated through Pd-catalyzed aryl and alkenyl C-N bond-forming reactions (see scheme; dba = dibenzylideneacetone). Amine, aniline, amide, carbamate, and sulfonamide functional groups can be introduced efficiently.
