146175-93-1Relevant articles and documents
Remote sp2C-H Carboxylation via Catalytic 1,4-Ni Migration with CO2
B?rjesson, Marino,Duan, Yaya,Janssen-Müller, Daniel,Martin, Ruben,Sahoo, Basudev,Wang, Xueqiang
supporting information, p. 16234 - 16239 (2020/10/09)
A remote catalytic reductive sp2 C-H carboxylation of arenes with CO2 (1 bar) via 1,4-Ni migration is disclosed. This protocol constitutes the first catalytic 1,4-Ni migration reported to date, thus offering new vistas in the Ni-catalyzed reductive coupling arena while providing an unconventional new platform for incorporating electrophilic sites at remote sp2 C-H linkages.
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.
Intramolecular Cycloadditions: Synthesis of 1-Methylene-2,3,3a,4,5,9b-hexahydro-1H-benzindenes and an unsuccessful approach to Ergot Alkaloids
Collins, Michael P.,Drew, Michael G. B.,Mann, John,Finch, Harry
, p. 3211 - 3218 (2007/10/02)
1-(1-Hydroxy-2-trimethylsilylmethylprop-2-enyl)-2-(4-substituted-but-3-enyl)-4-methoxybenzenes, prepared by a short synthesis, underwent intramolecular cycloadditions to produce the title indenes.An analogous intramolecular cycloaddition was attempte
Intramolecular (3+2) Cycloadditions
Collins, Michael P.,Mann, John,Capps, Nigel,Finch, Harry
, p. 239 - 240 (2007/10/02)
1-(1-Hydroxy-2-trimethylsilylmethylprop-2-enyl)-2-(4-methoxybut-3-enyl)-4-methoxybenzene, prepared by a short synthesis, underwent (3+2) cycloaddition to form predominantly the cis-fused tricycle 3,7-dimethoxy-1-methylene-2,3,3a,4,5,9b-hexahydro-1H-benze