1194-56-5Relevant articles and documents
Intramolecular heck reactions of unactivated alkyl halides
Firmansjah, Luke,Fu, Gregory C.
, p. 11340 - 11341 (2007)
A method has been developed for achieving palladium-catalyzed intramolecular Heck reactions of unactivated, β-hydrogen-containing alkyl bromides and chlorides. The data from a stereochemical investigation are consistent with carbon-carbon bond formation via an alkylpalladium, rather than a radical, intermediate. Copyright
The Manganese-Catalyzed Cross-Coupling Reaction and the Influence of Trace Metals
Santilli, Carola,Beigbaghlou, Somayyeh Sarvi,Ahlburg, Andreas,Antonacci, Giuseppe,Fristrup, Peter,Norrby, Per-Ola,Madsen, Robert
, p. 5269 - 5274 (2017/09/29)
The substrate scope of the MnCl2-catalyzed cross-coupling between aryl halides and Grignard reagents has been extended to several methyl-substituted aryl iodides by performing the reaction at elevated temperature in a microwave oven. A radical clock experiment revealed the presence of an aryl radical as an intermediate leading to the proposal of an SRN1 pathway for the coupling. The mechanistic information gave rise to suspicion about two previously published cross-coupling reactions catalyzed by manganese(II) salts. As a result, the coupling between aryl halides and organostannanes as well as between aryl halides and amines were revisited. Both reactions were found impossible to reproduce without the addition of small amounts of palladium or copper and are therefore not believed to be catalyzed by manganese.
Endo-selective pd-catalyzed silyl methyl heck reaction
Parasram, Marvin,Iaroshenko, Viktor O.,Gevorgyan, Vladimir
supporting information, p. 17926 - 17929 (2015/03/04)
A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.
Olefins turned alkylating agents: Diastereoselective intramolecular Zr-catalyzed olefin alkylations
Cesati III, Richard R.,De Armas, Judith,Hoveyda, Amir H.
, p. 395 - 398 (2007/10/03)
(Equation Presented) 62% yield; 12 : 1 syn : anti The first examples of intramolecular Zr-catalyzed electrophilic alkylation of aryl olefins are disclosed. Substituted carbo-and heterocycles are prepared efficiently and diastereoselectively.
A new catalytic transformation of diazo esters: hydride abstraction in dirhodium(II)-catalysed reactions
Doyle, Michael P.,Dyatkin, Alexey B.,Autry, Christopher L.
, p. 619 - 622 (2007/10/02)
Secondary benzylic and allylic diazoacetates undergo dirhodium(II)-catalysed diazo decomposition to form, competitively or exclusively, ketone and vinylidene products from intramolecular hydride abstraction in catalyst ligand-dependent molar ratios.
