6623-98-9Relevant academic research and scientific papers
Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides
Han, Chong,Buchwald, Stephen L.
supporting information; experimental part, p. 7532 - 7533 (2009/10/16)
(Chemical Equation Presented) An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired β-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool forC(sp3)-C(sp2) bond formation.
Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
Dreher, Spencer D.,Dormer, Peter G.,Sandrock, Deidre L.,Molander, Gary A.
supporting information; body text, p. 9257 - 9259 (2009/02/02)
Microscale parallel experimentation was used to discover three catalyst systems capable of coupling secondary organotrifluoroborates with sterically and electronically demanding aryl chlorides and bromides. The ensuing results represent the first comprehensive study of alkylboron coupling to aryl chlorides and, in particular, using secondary alkylboron partners. A ligand-dependent β-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases. Copyright
SUBSTITUTED PHENYLSULFAMOYL COMPOUNDS AS PPAR AGONISTS
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Page/Page column 65, (2010/11/28)
The present invention is directed at substituted phenylsulfamoyl compounds of Formula (I), pharmaceutical compositions containing such compounds and the use of such compounds as peroxisome proliferator activator receptor (PPAR) agonists. PPAR alpha activa
Electrochemical Reduction of Organic Compounds. 22. Preparation of Aromatic Aldehydes by Electroreduction of Esters and Amides in the Presence of Chlorotrimethylsilane
Goetz-Schatowitz, P.-R.,Struth, G.,Voss, J.,Wiegand, G.
, p. 230 - 234 (2007/10/02)
The electroreduction of aromatic esters 1 and amides 9 in dry acetonitrile in the presence of chlorotrimethylsilane 2 affords aldehydes 3 in moderate to good yields depending on the aromatic substituents.The formation of 3 and characteristic by-products is discussed.
13C magnetic resonance studies. 142. The fate of highly substituted acyclic ketones in strong base: β-enolization, Haller-Bauer cleavage, and an alkyl to aryl acyl shift
Dyllick-Brenzinger, Rainer A.,Patel, Vijay,Rampersad, Mollin B.,Stothers, J. B.,Thomas, Shirley E.
, p. 1106 - 1115 (2011/08/10)
Di-tert-butyl ketone (2a), 5,5,7,7-tetramethyl-6-undecanone (2b), and 2,4-dimethyl-2,4-diphenyl-3-pentanone (2d) have been found to undergo slow rearrangement by β-proton abstraction from the α-methyl groups upon treatment with t-BuO-/t-BuOH/>185 deg C.This is in contrast to the absence of such rearrangement in cyclic systems.It is the only significant process observed for 2a and 2b, whereas with 2d and its monomethyl analog 22 Haller-Bauer type cleavage and an unprecedented 1,3-acyl shift from sp3 to sp2 carbon accompany the β-enolate rearrangement.The rates of 1H/2H exchange of the methyl protons in 2a, b were found to be similar to those reported for a variety of cyclic systems but this exchange does not occur in 2d, where only aryl proton exchange was observed.
SYNTHESIS AND REARRANGEMENTS OF ALKYL-QUADRICYCLANONES
Figeys, H. P.,Destrebecq, M.,Lommen, G. Van
, p. 2369 - 2372 (2007/10/02)
Both 1-isopropyl-6- and 7-methoxycarbonyl-quadricyclanones, the first alkyl-substituted molecules of this type, have been synthesized.Cycloaddition reactions with methylpropiolate failed.Their different behaviour in rearrangement and degradation reactions
