510703-88-5Relevant articles and documents
Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling
Dennis, Joseph M.,White, Nicholas A.,Liu, Richard Y.,Buchwald, Stephen L.
supporting information, p. 4721 - 4725 (2018/04/11)
Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C-N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using 15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.
Aryne cycloaddition with 3-oxidopyridinium species
Ren, Hailong,Wu, Chunrui,Ding, Xiuxiu,Chen, Xiaoge,Shi, Feng
supporting information, p. 8975 - 8984,10 (2012/12/12)
The [3 + 2] cycloaddition of arynes with 3-oxidopyridinium species is examined using the Kobayashi benzyne precursor. The reaction affords a bicyclo[3.2.1] skeleton under mild conditions. A [7 + 2] cycloaddition mode with a subsequent pyridine ring-opening event has also been observed.
Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines
Kwong, Fuk Yee,Buchwald, Stephen L.
, p. 793 - 796 (2007/10/03)
(Matrix presented) An efficient copper-catalyzed amination of aryl bromides with primary alkylamines was developed that uses commercially available diethylsalicylamide as the ligand. This amination reaction can be performed at 90°C in good yield. A variety of functional groups are compatible with these reaction conditions. Preliminary results show that this reaction can be carried out under solvent-free conditions with comparable yields.