10219-31-5Relevant articles and documents
Benzyloxycalix[8]arene supported Pd-NHC cinnamyl complexes for Buchwald-Hartwig C-N cross-couplings
Abi Fayssal, Sandra,Buendia, Julien,Huc, Vincent,Martini, Cyril,Naret, Timothée,Schulz, Emmanuelle
, p. 5223 - 5231 (2021/08/16)
The scalable synthesis of Pd-NHC cinnamyl complexes supported on benzyloxycalix[8]arene is reported. These catalysts are very active for Buchwald-Hartwig cross-coupling reactions, allowing the coupling of aryl chlorides and bromides with a wide variety of alkyl and aryl amines using low catalytic loadings. The supported complexes also successfully afforded attractive unsymmetrical triarylamines, and in one case, promoted the synthesis of an unprecedented Pd-catalyzed C-H activation product. Thanks to the calixarenic support, the target products could be isolated with low levels of residual palladium, and in some cases, even below the restrictive toxic metal standards applied by the pharmaceutical industry. Through an easy to implement procedure, these perfectly characterised catalysts thus combine the best of homogeneous and heterogeneous catalysis: high efficiency (similar to or even better than the corresponding homogeneous complexes) and low Pd leaching levels expected from heterogeneous catalysts.
Copper-catalyzed N- tert -butylation of aromatic amines under mild conditions using tert -butyl 2,2,2-trichloroacetimidate
Cran, John W.,Vidhani, Dinesh V.,Krafft, Marie E.
, p. 1550 - 1554 (2014/07/08)
A variety of aromatic amines have been found to expediently undergo copper-catalyzed N-tert-butylation in the presence of tert-butyl 2,2,2-trichloroactimidate at room temperature. Georg Thieme Verlag Stuttgart New York.
Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
Samblanet, Danielle C.,Schmidt, Joseph A. R.
, p. 7 - 18,12 (2012/12/12)
While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.
