1245650-00-3Relevant academic research and scientific papers
A Micellar Catalysis Strategy for Suzuki-Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: No Copper, in Water, Very Mild Conditions
Isley, Nicholas A.,Wang, Ye,Gallou, Fabrice,Handa, Sachin,Aue, Donald H.,Lipshutz, Bruce H.
, p. 8331 - 8337 (2017/12/08)
Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.
Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides
Sakashita, Shohei,Takizawa, Miho,Sugai, Juugaku,Ito, Hajime,Yamamoto, Yasunori
supporting information, p. 4308 - 4311 (2013/09/24)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH 2CH2OH (20 mol %) in anhydrous DMF without bases.
Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of potassium 2-pyridyl trifluoroborate with aryl (heteroaryl) halides
Ren, Wei,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
, p. 1351 - 1358 (2012/03/10)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of potassium pyridine-2-trifluoroborates and various aryl (heteroaryl) halides can generate the corresponding desired coupling products with moderate to good yields. It can be carried out under the conditions with ethanol as solvent, Pd(OAc) 2 and SPhos as catalyst system and Na2CO3 as a base.
