Different Performance of Two Isomeric Phosphinobiphenyl Amidosulfonates in Pd-Catalyzed Cyanation of Aryl Bromides

نویسندگان

  • Jiří Schulz
  • Filip Horký
  • Kei Manabe
چکیده

A hydrophilic phosphinobiphenyl amidosulfonate, 2′-(dicyclohexylphosphino)-2{[(sulfonatomethyl)amino]carbonyl}[1,1′-biphenyl], triethylammonium salt (L2), was prepared and, together with its isomer bearing the polar amido-sulfonate tag in the position 4 of the biphenyl scaffold (compound L1), evaluated as a supporting ligand in Pd-catalyzed cyanation of aryl bromides using K4[Fe(CN)6] as the non-toxic cyanide source. The less sterically demanding ligand L1 was found to form more active catalysts than the newly prepared compound L2. A catalyst formed in situ from palladium(II) acetate and L1 efficiently mediated cyanation of aryl bromides bearing electron-donating substituents but failed in the analogous reactions with electron-poor substrates.

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

Palladium-catalyzed cyanation of aryl bromides promoted by low-level organotin compounds.

A novel method for palladium-catalyzed cyanation of aryl bromides promoted by low-level tri-n-butyltin chloride or cyanide is described. The method features low catalyst loading and mild reaction conditions. KCN is used as the cyanide source. Only trace levels of the tri-n-butyltin compound are required to achieve high conversion and yield in the cyanation of aryl bromides, iodides, and triflates.

متن کامل

Synthesis, Structural Characterization and Catalytic Evaluation of Anionic Phosphinoferrocene Amidosulfonate Ligands

Triethylammonium salts of phosphinoferrocene amidosulfonates with electron-rich dialkyphosphino substituents, R2PfcCONHCH2SO3(HNEt3) (4a–c), where fc = ferrocene-1,1′-diyl, and R = i-Pr (a), cyclohexyl (Cy; b), and t-butyl (c), were synthesized from the corresponding phosphinocarboxylic acids-borane adducts, R2PfcCO2H·BH3 (1a–c), via esters R2PfcCO2C6F5·BH3 (2a–c) and adducts R2PfcCONHCH2SO3(HN...

متن کامل

An expedient Pd/DBU mediated cyanation of aryl/heteroaryl bromides with K4[Fe(CN)6].

A practical Pd(PPh(3))(4)/DBU catalytic system for the synthesis of pharmaceutically relevant aminopyridine nitrile intermediates, as well as a variety of other aryl nitriles using non-toxic K(4)[Fe(CN)(6)] has been developed. The key features of our new protocol for cyanation lie in that the reaction can be carried out with readily available Pd(PPh(3))(4) under mild and green conditions, even ...

متن کامل

A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides.

Playing it safe: The nontoxic cyanide source K4 [Fe(CN)6]·3H2O can be used for the cyanation of (hetero)aryl halides. The application of palladacycle catalysts prevents poisoning during catalyst formation, thereby allowing for low catalyst loadings, fast reaction times, and wide heterocyclic substrate scope.

متن کامل

Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes

We report the Pd-catalyzed α-arylation of α,α-difluoroketones with aryl and heteroaryl bromides and chlorides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)Cy2 as ligand. The combination of this Pd-catalyzed arylation and base-induced cleavage of the acyl-aryl C-C bond within the α-aryl-α,α-difluoroketone constitutes a one-pot, two-step procedure to synthesize...

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 2016