167367-47-7Relevant academic research and scientific papers
Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles
Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 946 - 950 (2014/04/03)
A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.
Synthesis of 2-aryl-substituted chromans by intramolecular C-O bond formation
Wang, Yu,Franzén, Robert
, p. 925 - 929 (2012/06/15)
A synthetic route for the preparation of 2-aryl-substituted chromans from commercially available starting materials and utilizing either a palladium- or copper-catalyzed intramolecular cyclization of aryl bromides is described. Chromans with stereocontrol at C-2 can thus be obtained via a palladium-catalyzed asymmetric allylic etherification procedure utilizing a chiral indole-phosphine oxazoline (IndPHOX) ligand. Georg Thieme Verlag Stuttgart · New York.
Palladium-catalyzed tandem reactions to form 1-vinyl-1H-isochromene derivatives
Mutter,Campbell,de la Nava,Merritt,Wills
, p. 3284 - 3290 (2007/10/03)
The palladium-catalyzed reaction of pinacolone with tert-butyldimethyl(3-(2-bromophenyl)allyloxy)-silane results in direct formation of 1-vinyl-3-tert-butyl-1H-isochromene. This is the result of a ketone arylation followed by an intramolecular cyclization of the enolate with the allylic system. The use of a lithium diamide base appears to be essential for success. The tert-butyldimethylsilyl protecting group is also an essential choice as it furnishes the appropriate reactivity to promote allylic substitution after the aryl coupling process. The use of more effective leaving groups, such as acetate, results in reaction of the allylic group, and no aryl coupling is observed. Through the appropriate selection of phosphine ligand and solvent, either the cyclized isochromene product or the noncyclized intermediate may be formed selectively. A short combinatorial study of the scope and limitations of the reaction, involving 24 ketones, is described.
Asymmetric Induction in the Electrocyclisations of 1,3 Dipolar Intermediates: the 1.7 Cyclisation of Diene-conjugated Diazo-compounds to give 1H-2,3-Benzodiazepines
Blake, Alexander J.,Harding, Mervyn,Sharp, John T.
, p. 3149 - 3162 (2007/10/02)
In the cyclisation of the diene-conjugated diazo compounds 4 to give the diastereomeric pair of 1H-2,3-benzodiazepines 7 and 8, alkyl and silyl ethers when present as the 'medium' sized group R3, showed the opposite effect in controlling face selectivity
