Bromination of Ketones by Palladium(II). An Asymmetric α-Bromoketones Catalytically Synthesized by a Mono Palladium(II) Catalyst

نویسندگان

  • Arab K. El-Qisairi
  • Hanan A. Qaseer
چکیده

The oxidation of ketones by monometallic [Pd(CH3CN)2(S)-Tol-BINAP](BF4)2 A or [Pd(CH3CN)2(S)-METBOX](BF4)2 B in aqueous THF containing copper(II) bromide produced chiral α-bromoketones. The α-bromoketone products were obtained with moderate to high enantiomeric excess (68-89% ee) and good isolated yields (70-90%). The highest optical purities were 89% ee for cycloheptanone. Catalyst B gave slightly higher enantioselectivities than catalyst A. All symmetric ketones gives only one product whereas, oxidation of 2-butanone gives the 3-bromo-2-butanone and 1-bromo-2-butanone. The α-bromoketone products were characterized by FTIR, H, C-NMR and GC/MS.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

A highly active and selective palladium pincer catalyst for the formation of α-aryl ketones via cross-coupling.

Several air and moisture stable Pd(II) pincer complexes were synthesized via oxidative addition of Pd(0) to novel PheBox pincer ligand precursors. Low loadings (1 mol%) of the Pd complex [t-BuPhebox-Me(2)]PdBr are capable of efficiently promoting the selective α-monoarylation of a variety of ketones with numerous aryl bromides in only 1 h at 70 °C with 82-99% yields.

متن کامل

Synthesis of nanostructured palladium, palladium oxide and palladium-palladium oxide nanocomposite by the gel combustion method and application as catalyst of hydrogen release

This paper presents a new gel combustion method to synthesize palladium nanoparticles, palladium oxide (PdO) nanoparticles and palladium-palladium oxide nanocomposites. In the proposed method, there are some effective parameters including palladium chloride concentration, polyvinyl alcohol (PVA) concentration, acid concentration, solvent composition and combustion temperature that their values ...

متن کامل

Theoretical study on the mechanism of hydromethoxylation catalyzed by palladium(II) complex

Palladium (II) coordination complexes catalyze the reaction of alcohols with ketones to yield ethers. During the catalytic cycle, the alcohol adds selectively to the β-carbon (anti-Markovnikov). In this work, mechanism and kinetics for the reaction of methanol with methyl vinyl ketone (MVK), being catalyzed by Pd, has been theoretically investigated in detail. Using quantum mechanical approach,...

متن کامل

Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Palladium is arguably the most versatile and most widely applied catalytic metal in the field of fine chemicals due to its high selectivity and activity. Palladium catalyst offers an abundance of possibilities of carbon-carbon bond formation in organic synthesis. In this research, three different Schiff base ligands have been prepared by condensation reaction between appropriate aldehyde or ket...

متن کامل

Theoretical study on the mechanism of hydromethoxylation catalyzed by palladium(II) complex

Palladium (II) coordination complexes catalyze the reaction of alcohols with ketones to yield ethers. During the catalytic cycle, the alcohol adds selectively to the β-carbon (anti-Markovnikov). In this work, mechanism and kinetics for the reaction of methanol with methyl vinyl ketone (MVK), being catalyzed by Pd, has been theoretically investigated in detail. Using quantum mechanical approach,...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2007