398-66-3Relevant academic research and scientific papers
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.
Direct intermolecular aniline ortho- arylation via benzyne intermediates
Truong, Thanh,Daugulis, Olafs
supporting information, p. 5964 - 5967 (2013/02/22)
A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.
Palladium- and nickel-catalyzed aminations of aryl imidazolylsulfonates and sulfamates
Ackermann, Lutz,Sandmann, Rene,Song, Weifeng
supporting information; experimental part, p. 1784 - 1786 (2011/06/10)
A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.
