Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions
نویسندگان
چکیده
The Pd-benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji-Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.
منابع مشابه
Synthesis of Functionalized Hydrazines: Facile Homogeneous (N‐Heterocyclic Carbene)‐Palladium(0)‐Catalyzed Diboration and Silaboration of Azobenzenes
The bis(N-heterocyclic carbene)(diphenylacetylene)palladium complex [Pd(ITMe)2(PhC≡CPh)] (ITMe=1,3,4,5-tetramethylimidazol-2-ylidene) acts as a highly active pre-catalyst in the diboration and silaboration of azobenzenes to synthesize a series of novel functionalized hydrazines. The reactions proceed using commercially available diboranes and silaboranes under mild reaction conditions.
متن کاملEfficient Suzuki and Sonogashira coupling reactions catalyzed by Pd/DNA@MWCNTs in green solvents and under mild conditions
The palladium nanoparticles were immobilized on DNA-modified multi walled carbon nanotubes as stable and powerful heterogeneous catalyst. The catalyst was characterized by FT-IR spectroscopy, UV-Vis spectroscopy, field emission scanning electron microscopy, X-ray diffraction, transmission electron microscopy, inductively coupled plasma and elemental analysis. DNA as a well-defined structure and...
متن کاملDeacylative allylation of nitroalkanes: unsymmetric bisallylation via 3-component coupling
Catalytic Tsuji-Trost allylation has become a ubiquitous method for allylation of active methylene compounds.[1] While monoallylation products are typically formed, bisallylation of malonates and related ketone enolates leads to 1,6-dienes.[2] Given the utility of these 1,6heptadienes in metal-catalyzed cycloisomerization reactions,[3] it would be beneficial if one could perform controlled bisa...
متن کاملRegiospecific decarboxylative allylation of nitriles.
Palladium-catalyzed decarboxylative alpha-allylation of nitriles readily occurs with use of Pd(2)(dba)(3) and rac-BINAP. This catalyst mixture also allows the highly regiospecific alpha-allylation of nitriles in the presence of much more acidic alpha-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, m...
متن کاملPyridyl-supported pyrazolyl-N-heterocyclic carbene ligands and the catalytic activity of their palladium complexes in Suzuki-Miyaura reactions.
Palladium complexes of two new types of unsymmetrical pyridyl-supported pyrazolyl-N-heterocyclic carbene ligands were synthesized and structurally characterized. A strategy to release the steric strain of the ligand was realized by the introduction of methylene linkers to the ligand molecule. All the palladium complexes exhibited good to excellent catalytic activity in Suzuki-Miyaura reactions ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 11 شماره
صفحات -
تاریخ انتشار 2015