63558-71-4Relevant academic research and scientific papers
Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides
Ge, Shaozhong,Hartwig, John F.
supporting information, p. 12837 - 12841 (2013/02/22)
One for all: The coupling of a range of nitrogen- and sulfur-containing heteroaryl halides with five-membered nitrogen-, oxygen-, and sulfur-containing heteroaryl boronic acids were achieved in high yields with only 0.5 mol % of the single-component nickel precatalyst [(dppf)NiCl(cinnamyl)] (dppf=1,1′- bis(diphenylphosphanyl)ferrocene). The reaction demonstrates good functional group compatibility, and is easily conducted on a large scale without a dry box. Copyright
Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan
Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo
supporting information; experimental part, p. 3255 - 3266 (2011/02/23)
A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert- butylphenylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand. Copyright
Solvent-free, palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl chlorides with arylboronic acids
Li, Jin-Heng,Deng, Chen-Liang,Xie, Ye-Xiang
, p. 2433 - 2448 (2008/02/10)
Pd(MeCN)2Cl2/PCy3 was found to be an efficient catalytic system for the Suzuki-Miyaura cross-couplings of aryl chlorides with arylboronic acids under solvent-free conditions. Furthermore, the presence of the conventional solvents had deleterious effect on the reaction. In the presence of Pd(MeCN)2Cl2, PCy3, and TBAF (tetra-n-butylammonium fluoride), a number of aryl chlorides including heteroaryl chlorides were coupled with arylboronic acids or heteroarylboronic acids smoothly to afford the corresponding products in moderate to excellent yields. Copyright Taylor & Francis Group, LLC.
Pd(OAc)2/DABCO-catalyzed Suzuki-Miyaura cross-coupling reaction in DMF
Li, Jin-Heng,Zhu, Qi-Ming,Xie, Ye-Xiang
, p. 10888 - 10895 (2007/10/03)
The scope and limitations of the Pd(OAc)2/DABCO (1,4-diaza-bicyclo[2.2.2]octane)-catalyzed Suzuki-Miyaura cross-coupling reactions have been demonstrated. The results showed that the effect of solvent had a fundamental influence on the reaction. In the presence of Pd(OAc)2 and DABCO, both aryl bromides and aryl chlorides all worked well with arylboronic acids to form biaryls, heteroaryl-aryls, and biheteroaryls in moderate to excellent yields using DMF as the solvent. Additionally, the reactions of aryl bromides were conducted under relatively mild conditions.
