503274-02-0Relevant academic research and scientific papers
Mechanism of the Palladium-Catalyzed Synthesis of Münchnones: The Role of Ligands in N-Acyl Iminium Salt Carbonylation
Tjutrins, Jevgenijs,Dhawan, Rajiv,Lu, Yingdong,Arndtsen, Bruce A.
supporting information, p. 15945 - 15954 (2016/10/24)
The palladium-catalyzed carbonylative coupling of imines, acid chlorides, and dipolarophiles can provide efficient routes to prepare nitrogen-containing heterocycles. One challenge in developing this reaction, and in the creation of more active catalyst systems, is the lack of data on how this complex transformation proceeds. To address this, we report here the results of our mechanistic studies on this system, and in particular the formation of mesoionic münchnones. This includes the synthesis of key catalytic intermediates, model reactions, and kinetic studies that support the role of these compounds in catalysis. Together, these studies provide a clear picture of the impact of catalyst structure, ligands, and palladium nanoparticles on facilitating the carbonylation of in situ generated iminium salts, and suggest an avenue for the creation of more active catalyst systems.
Palladium-Catalyzed Multicomponent Coupling of Alkynes, Imines, and Acid Chlorides: A Direct and Modular Approach to Pyrrole Synthesis
Dhawan, Rajiv,Arndtsen, Bruce A.
, p. 468 - 469 (2007/10/03)
A new palladium-catalyzed method to prepare pyrroles directly from three basic building blocks - imines, alkynes, and acid chlorides - is described. This approach provides a straightforward method both to prepare pyrroles in one step and to diversify their structure by simple variation of any of the three starting materials. Mechanistic studies suggest that this process occurs via a complex series of eight individual steps, and this is discussed. Copyright
