33930-75-5Relevant academic research and scientific papers
Synthesis of dihydroisoquinolinone-4- methylboronic esters via domino Heck/borylation using a structurally characterized palladacycle as a catalyst
Morla, Jhansi Rani,Nareddula, Dastagiri Reddy
, p. 6762 - 6771 (2022/03/31)
Synthesis of dihydroisoquinolinone-4-methylboronic esters from N-allylcarboxamides and B2(Pin) 2via domino Heck/borylation approach is reported. A quinoxaline-based NHC-palladacycle [Pd(C^C:)PPh3Cl], which has been structurally characterized, is used as a catalyst. The scope of the substrate with a wide range of substituents is explored. In addition to the synthesis of title compounds, a few examples of methylboronic esters of indoline and benzofuran motifs have also been prepared using the same protocol.
New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure. Isolation and characterization of σ-alkylpalladium Heck intermediates
Beccalli, Egle M.,Broggini, Gianluigi,Martinelli, Michela,Masciocchi, Norberto,Sottocornola, Silvia
, p. 4521 - 4524 (2007/10/03)
A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/ intramolecular Heck reaction/1,3-dipolar
Nitrogen ligands: The transition metal catalyzed reaction of aryl halides with olefins (Mizoroki-Heck), phenylboronic acid (Suzuki coupling) and Buchwald-Hartwig amination, new catalysts and effect of co-catalysts - Aryl halide activation - Part I
Iyer, Suresh,Kulkarni, Girish M.,Ramesh,Sattar, Aruna K.
, p. 1894 - 1908 (2007/10/03)
Nitrogen ligands are an excellent alternative for the traditional P-ligands in the Pd catalyzed Mizoroki-Heck reaction, Suzuki coupling and Buchwald-Hartwig aryl amination. Pd complexes of dimethyl glyoxime, 8-hydroxyquinoline, salen, picolinic acid, and DAB ligands gave high yields of the E-cinnamates and E-stilbenes from aryl iodides. Acetophenone oxime N, N-dimethybenzylamine and ferrocenyl oxime palladacycle are better catalysts with comparable yields, high TON (95, 000) and TOF's (2, 500 h-1) to P-ligand catalysts. Aryl bromides and in a few cases, aryl chlorides could also be activated by these complexes by the use of Lewis acid and (C 4H9)4NI as additives. Cy-DAB ligands gave good yields with electron rich aryl bromides and the use of ionic liquid improve the yield. These N-ligand metal complexes can be readily synthesized and the ligands possess the advantage of easy functional group modifications and convenient synthetic methods compared to P-ligands. The degradation reactions associated with P-ligands are not observed in the N-ligands, with comparable, high thermal, moisture and air stability and insensitivity. Activation of aryl bromides (Mizoroki-Heck reaction, Suzuki reaction) could be achieved in high yields, TON and TOF (86-94% yield, TON: 36, 000-90, 000, TOF: 6, 000-11, 500 h-1) catalyzed by monomeric amine and oxime palladacycles (Cat-8, 11, 13 B) with a N-heterocyclic carbene ligand better than a phosphorous ligand. Molten (C 4H9)4NBr is an efficient ionic liquid medium for the Mizoroki-Heck reaction of aryl bromides, giving higher yields. Low to moderate yields of aryl amination are obtained with the carbene palladacycle and N, N-dibenzyl piperazine Pd complexes.
Ni(O) catalyzed reactions of aryl and vinyl halides with alkenes and alkynes
Iyer, Suresh,Ramesh, Chinnasamy,Ramani
, p. 8533 - 8536 (2007/10/03)
NI[P(OPh)3]4 and Ni[P(OET)3]4 catalyze the reaction of aryl and vinyl halides with olefins (Heck reaction) and alkynes.
The vinylation of aryl and vinyl halides catalyzed by copper salts
Iyer, Suresh,Ramesh, Chinnasamy,Sarkar, Anjana,Wadgaonkar, Prakash P.
, p. 8113 - 8116 (2007/10/03)
Copper (I) bromide and copper (I) iodide catalyzed the vinylation of aryl and vinyl iodides to give the corresponding vinylated products in good to high yields.
NMR-Spectroskopische Untersuchung von Isocumarin- und Isocarbostyril-Derivaten
Duddeck, Helmut,Kaiser, Manfred
, p. 913 - 924 (2007/10/02)
The syntheses and the 1H, 13C and 15N NMR spectra of 47 isocumarin and isocarbostyril derivatives are reported and discussed.The data include T1 relaxation times and geometries of some complexes with Yb(dpm)3.
Thioenamide Photochemistry
Couture, Axel,Dubiez, Regine,Lablache-Combier, Alain
, p. 842 - 843 (2007/10/02)
In contrast with their oxo-analogues, thioenamides undergo photochemical cyclization to yield isoquinolinethione derivatives which are easily converted into isoquinolones and tetrahydroisoquinolines by treatment with benzeneseleninic anhydride and EtO3BF4
