325147-50-0Relevant academic research and scientific papers
Direct Access to N-tert-Butanesulfinyl Imines from Aryl Iodides, Alkenyl Alcohols, and N-tert-Butanesulfinamide
Ikhlef, Sofiane,Behloul, Cherif,Lahosa, Alejandro,Foubelo, Francisco,Yus, Miguel
, p. 2609 - 2614 (2018/05/03)
The reaction of aryl iodides, N-tert-butanesulfinamide, and allyl or homoallyl alcohol in the presence of a catalytic amount of Pd(OAc)2, NaHCO3 as a base, and TBAB leads to the formation of N-tert-butanesulfinyl imines in moderate yields. In this one-pot process, a sequential Heck-type arylation of the alkenol, isomerization of the double bond, and imine formation take place.
Synthesis of tetrasubstituted alkenes through a palladium-catalyzed domino carbopalladation/C-H-activation reaction
Tietze, Lutz F.,Hungerland, Tim,Duefert, Alexander,Objartel, Ina,Stalke, Dietmar
supporting information; experimental part, p. 3286 - 3291 (2012/04/17)
Helical tetrasubstituted alkenes (7) were obtained in a highly efficient way through a palladium-catalyzed domino-carbopalladation/CH-activation reaction of propargylic alcohols 6 in good to excellent yields. Electron-withdrawing- and electron-donating substituents can be introduced onto the upper and lower aromatic rings. The substrates (6) for the domino process were synthesized by addition of the lithiated alkyne (20) to various aldehydes (19); moreover, the substrates were accessible enantioselectively (in 95 % ee) by reduction of the corresponding ketone using the Noyori procedure. Copyright
Unsymmetrical biaryls by palladium-catalyzed coupling of aryl halides with internal reduction
Satyanarayana, Gedu,Maier, Martin E.
scheme or table, p. 5543 - 5552 (2009/05/11)
Aryl bromides containing a (1,4,5,6-tetrahydro-6-oxopyridin-3-yl)methyl substituent can be coupled with aryl halides yielding unsummetrical biaryls. In the course of this process, the cyclic enamide is oxidized to the 2(1H)-pyridinone. The reaction procee
Biaryl formation from 5-(2-bromobenzyl)-substituted piperidin-2-ones via palladacycles
Satyanarayana, Gedu,Maier, Martin E.
scheme or table, p. 2361 - 2364 (2009/05/27)
(Chemical Equation Presented) The reaction of piperdin-2-ones with a 2-bromobenzyl substituent in the 5-position in the presence of a palladium catalyst leads to biaryl compounds. Their formation can be explained via initial C-H insertion of the aryl pall
Synthesis of 1,5-methano-3-benzazocines by intramolecular Buchwald-Hartwig arylation of 2-piperidinones
Satyanarayana, Gedu,Maier, Martin E.
, p. 356 - 363 (2008/04/01)
A conceptually novel route to 1,5-methano-3-benzazocines based on an intramolecular Buchwald-Hartwig arylation was developed. The reaction required the use of the zinc enolate of the piperidinone substrates. These substrates, piperidin-2-ones with a 2-bro
Palladium-catalyzed intramolecular C-O bond formation
Kuwabe,Torraca,Buchwald
, p. 12202 - 12206 (2007/10/03)
A number of oxygen heterocycles were synthesized using the palladium-catalyzed intramolecular etherification of aryl halides by employing di-tert-butylphosphinobiaryl ligands. The reaction proceeds under mild conditions using weak bases such as Cs2CO3 or K3PO4. A variety of functional groups are tolerated in the reaction, and enantioenriched alcohols can be coupled without erosion of optical purity. The mildness of the reaction conditions allows for the use of polyfunctionalized substrates. This method was used as the key step in the synthesis of MKC-242, an antidepressant currently in clinical trials. The synthesis of MKC-242 was achieved in 40% overall yield from commercially available sesamol and acrylonitrile.
