4791-89-3Relevant academic research and scientific papers
A Copper-Catalyzed Reductive Defluorination of β-Trifluoromethylated Enones via Oxidative Homocoupling of Grignard Reagents
Wu, Xiaoting,Xie, Fang,Gridnev, Ilya D.,Zhang, Wanbin
, p. 1638 - 1642 (2018/03/23)
An efficient copper-catalyzed reductive defluorination of β-trifluoromethylated enones via an oxidative homocoupling of Grignard reagents is reported. The reaction proceeded smoothly with a wide range of substrates, including the ones bearing aromatic heterocycles, such as furyl and thienyl ring systems in high yields (80-92%, except one example) under mild conditions. This provides a practical method for synthesis of gem-difluoroolefin ketones. It is also worth noting that this homocoupling process of Grignard reagents using β-trifluoromethylated enones as oxidizing reagents is effective for both the Csp2-Csp2 and Csp3-Csp3 bond formations, including for substrates whose β-hydride elimination of the corresponding transition metal alkyl complex is particularly facile, affording coupling products with high yields (83-95%), simultaneously.
Nickel-catalyzed synthesis of diarylamines via oxidatively induced C-N bond formation at room temperature
Ilies, Laurean,Matsubara, Tatsuaki,Nakamura, Eiichi
supporting information, p. 5570 - 5573,4 (2012/12/12)
A nickel-catalyzed oxidative coupling of zinc amides with organomagnesium compounds selectively produces diarylamines under mild reaction conditions, with tolerance for chloride, bromide, hydroxyl, ester, and ketone groups. A diamine is bis-monoarylated. A bromoaniline undergoes N-arylation followed by Kumada-Tamao-Corriu coupling in one pot. The reaction may proceed via oxidatively induced reductive elimination of a nickel species.
Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts
Schmidt, Bernd,Hoelter, Frank
supporting information; experimental part, p. 4914 - 4920 (2011/08/06)
The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis. The Royal Society of Chemistry 2011.
5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly reactive and recoverable organo-bismuth reagents for cross-coupling reactions with Aryl Bromides
Shimada, Shigeru,Yamazaki, Osamu,Tanaka, Toshifumi,Rao, Maddali L. N.,Suzuki, Yohichi,Tanaka, Masato
, p. 1845 - 1848 (2007/10/03)
Hypervalent organobismuth compounds efficiently couple with aryl bromides in the presence of [Pd(PPh3)4] catalyst. Application of this protocol to a one-pot multi-coupling reaction with bromophenylboronic esters leads to the formation of up to nine bonds in good yields (see scheme).
Palladium/P(t-Bu)3-catalyzed synthesis of aryl t-butyl ethers and application to the first synthesis of 4-chlorobenzofuran
Watanabe, Makoto,Nishiyama, Masakazu,Koie, Yasuyuki
, p. 8837 - 8840 (2007/10/03)
Pd/P(t-Bu)3 catalyzed reaction of aryl halides with sodium t-butoxide effectively to give aryl t-butyl ethers. The high catalytic activity realized the formation of aryl t-butyl ethers from not only electron-deficient aryl halides but also electron-rich aryl halides. Moreover, the first synthesis of 4-chlorobenzofuran was attained utilizing the selective mono-t-butoxylation of aryl dihalide.
Convergent Routes to the Dioxolophenanthridin-6(5H)-one and 2,3,4,4a-Tetrahydrodioxolophenanthridin-6(5H)-one Nuclei. Application to Syntheses of the Amaryllidaceae Alkaloids Crinasiadine, N-Methylcrinasiadine and Trisphaeridine
Banwell, Martin G.,Cowden, Cameron J.
, p. 2235 - 2254 (2007/10/02)
Convergent routes to the title nuclei, (1) and (6), have been developed.Thus, Suzuki coupling of boronic acid (8) with aryl bromide (9) gave the biarylylcarbamate (7) which, on treatment with phosphorus oxychloride (POCl3), underwent Bischler-Napieralski
