Microwave-enhanced synthesis of aryl nitriles using dimeric orthopalladated complex of tribenzylamine and K4[Fe(CN)6]

Published on Feb 1, 2012in Tetrahedron Letters2.415
· DOI :10.1016/J.TETLET.2011.11.087
Abdol R. Hajipour41
Estimated H-index: 41
 (IUT: Isfahan University of Technology), Fatemeh Rafiee17
Estimated H-index: 17
 (IUT: Isfahan University of Technology), Arnold E. Ruoho52
Estimated H-index: 52
 (UW: University of Wisconsin-Madison)
Sources
Abstract
Abstract The activity of palladacycle [Pd{C 6 H 4 (CH 2 N(CH 2 Ph) 2 )} (μ-Br)] 2 complex was investigated in the synthesis of benzonitriles under both conventional and microwave irradiation conditions and their results were compared together. This complex is an efficient, stable, and non-sensitive to air and moisture catalyst for the cyanation reaction. The substituted benzonitriles were produced of various aryl halides in excellent yields and short reaction times using a catalytic amount of [Pd{C 6 H 4 (CH 2 N(CH 2 Ph) 2 )} (μ-Br)] 2 complex and K 4 [Fe(CN) 6 ] in DMF at 130 °C. In comparison to conventional heating conditions, the reactions under microwave irradiation gave higher yields in shorter reaction times.
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References39
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Sep 14, 2011·Tetrahedron Letters2.42
#1Abdol R. Hajipour (IUT: Isfahan University of Technology)H-Index: 41
#2Fatemeh Rafiee (IUT: Isfahan University of Technology)H-Index: 17
Last. Arnold E. Rouho (UW: University of Wisconsin-Madison)H-Index: 1
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Abstract The [Pd{C 6 H 2 (CH 2 CH 2 NH 2 )-(OMe) 2 ,3,4}Br(PPh 3 )] monomeric orthopalladate complex of homoveratrylamine and triphenylphosphine was synthesized and its application in Heck coupling reactions was investigated. This complex had been demonstrated to be more active than the corresponding dimeric catalyst for Heck reactions of aryl iodides, bromides and even chlorides and also arenesulfonyl chlorides. The cross-coupled products were produced in excellent yields using catalytic amount...
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Aug 1, 2011·Applied Organometallic Chemistry4.11
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Kazem Karami (IUT: Isfahan University of Technology)H-Index: 22
Last. Ghazal Tavakoli (IUT: Isfahan University of Technology)H-Index: 13
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The activity of [Pd(C6H4CH2NH2-κ2-C-N)PPh3MOBPPY]OTf complex, A (MOBPPY = 4-methoxybenzoylmethylenetriphenylphosphoraneylide) was investigated in the homocoupling reaction of a vast range of aryl halides under both conventional and microwave irradiation conditions and their results were compared. The complex was active and showed high efficiency in the formation of new C-C bonds. The yields were excellent using a catalytic amount of [Pd(C6H4CH2NH2-κ2-C-N)PPh3MOBPPY]OTf complex in N, N-dimethylfo...
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Jul 1, 2011·Applied Organometallic Chemistry4.11
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Fatemeh Rafiee (IUT: Isfahan University of Technology)H-Index: 17
The activity of {Pd[C6H2(CH2CH2NH2)-(OMe)2,3,4] (µ-Br)}2 complex was investigated in the Heck–Mizoroki CC cross-coupling reaction under conventional heating and microwave irradiation conditions in molten salt tetrabutylammonium bromide as the solvent and promoter at 130 °C. This complex in these conditions is an active and efficient catalyst for the Heck reaction of aryl iodides, bromides and even chlorides, and also arenesulfonyl chlorides. Copyright © 2011 John Wiley & Sons, Ltd.
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Jul 1, 2011·Journal of Organometallic Chemistry2.37
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Fatemeh Rafiee (IUT: Isfahan University of Technology)H-Index: 17
Abstract The activity of [Pd{C 6 H 4 (CH 2 N(CH 2 Ph) 2 )} (μ-Br)] 2 complex was investigated in the Heck–Mizoroki C–C cross-coupling reaction. This complex is an active and efficient catalyst for the Heck reaction of aryl iodides, bromides and even chlorides and also arenesulfonyl chlorides. The cross-coupled products were produced in excellent yields in short reaction time using a catalytic amount of [Pd{C 6 H 4 (CH 2 N(CH 2 Ph) 2 ) (μ-Br)] 2 complex in NMP at 130 °C.
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May 15, 2011·Inorganica Chimica Acta2.54
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Kazem Karami (IUT: Isfahan University of Technology)H-Index: 22
Last. Azadeh Pirisedigh (IUT: Isfahan University of Technology)H-Index: 10
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Abstract The Suzuki–Miyaura reaction of various aryl halides using [Pd{C 6 H 2 (CH 2 CH 2 NH 2 )–(OMe) 2 ,3,4} (μ-Br)] 2 have been investigated. This orthopalladated complex is an efficient, stable and non-sensitive to air and moisture catalyst for the hetrocoupling reaction in DMF as the reaction solvent at 130 °C. The combination of dimeric complex as homogenous catalyst and microwave irradiation can be very useful and efficient methods in organic synthesis, so the application of microwave irr...
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Mar 3, 2011·Synthetic Communications2.01
#1Martin BeckerH-Index: 6
#2Axel SchulzH-Index: 54
Last. Karsten VossH-Index: 8
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Abstract Modification of Beller's palladium-catalyzed cyanation procedure leads to a versatile and rapid route to poly-nitrile aromatics via easily available aryl bromides that improve on known literature methods. All cyanide ions on the iron(II) center of the nontoxic cyanide source [potassium hexacyanoferrate(II)] can be transferred to the aryl halide using palladium(II) acetate and 1,1′-bis(diphenylphosphino)ferrocen (dppf).
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Feb 15, 2011·Journal of Organometallic Chemistry2.37
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Kazem Karami (IUT: Isfahan University of Technology)H-Index: 22
Last. Azade Pirisedigh (IUT: Isfahan University of Technology)H-Index: 1
view all 4 authors...
Abstract Application of a new catalytic system for cyanation reaction of various aryl halides using K 4 [Fe(CN) 6 ] as cyanating source was examined. The reactions were performed under microwave irradiation and results showed that application of this catalytic system and DMF at 130 °C minimized the reaction times from hours to minutes in good to excellent yields.
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Nov 1, 2010·Applied Organometallic Chemistry4.11
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Kazem Karami (IUT: Isfahan University of Technology)H-Index: 22
Last. Ghazal Tavakoli (IUT: Isfahan University of Technology)H-Index: 13
view all 3 authors...
The activity of [Pd(C6H4CH2 NH2-κ2-C-N)PPh3MOBPPY]OTf complex, A (MOBPPY = 4-methoxybenzoylmethylenetriphenyl- phosphoraneylide), was investigated in the Heck–Mizoroki CC cross-coupling reaction under conventional heating and microwave irradiation conditions. The complex is an active and efficient catalyst for the Heck reaction of aryl halides. The yields were excellent using a catalytic amount of [Pd(C6H4CH2 NH2-κ2-C-N)PPh3MOBPPY]OTf complex in N-methyl-2-pyrrolidinone (NMP) at 130 °C and 600 W...
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Oct 1, 2010·Journal of Organometallic Chemistry2.37
#1Manirul Islam (KGEC: Kalyani Government Engineering College)H-Index: 13
#2Paramita Mondal (KGEC: Kalyani Government Engineering College)H-Index: 20
Last. Dilder Hossain (KGEC: Kalyani Government Engineering College)H-Index: 4
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Abstract An inexpensive, air–moisture stable and reusable PS–Pd(II)–anthra complex was synthesized by reacting chloro-methylated polystyrene with anthranilic acid to get polymer anchored ligand which was then reacted with PdCl 2 to get polymer anchored complex. This complex was characterized by different spectroscopic and elemental analyses. The activity of the Pd-complex as catalyst was tested for the Suzuki, Heck, Sonogashira cross-coupling and also for amination and cyanation reactions under ...
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Jun 1, 2010·Applied Organometallic Chemistry4.11
#1Abdol R. Hajipour (UW: University of Wisconsin-Madison)H-Index: 41
#2Kazem Karami (IUT: Isfahan University of Technology)H-Index: 22
Last. Azadeh Pirisedigh (IUT: Isfahan University of Technology)H-Index: 10
view all 3 authors...
An efficient method for preparation of aryl nitriles—using [Pd{C6H2(CH2CH2 NH2)-(OMe)2,3,4} (µ-Br)]2 complex as an efficient catalyst and K4[Fe(CN)6] as a green cyanide source—from aryl bromides, aryl iodides and aryl chlorides under microwave irradiation has been reported. This complex has been demonstrated to be an active and efficient catalyst for this reaction. Using a catalytic amount of this synthesized palladium complex in DMF at 130 °C led to production of the cyanoarenes in excellent yi...
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#1Alexander M. Nauth (University of Mainz)H-Index: 10
#2Till Opatz (University of Mainz)H-Index: 35
The present review gives an overview over non-toxic cyanation agents and cyanide sources used in the synthesis of structurally diverse products containing the nitrile function. Nucleophilic as well as electrophilic agents/systems that transfer the entire CN-group were taken in consideration. Reactions in which a preexisting carbon functionality is transformed into a nitrile function by addition of nitrogen are however not covered here.
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The catalytic activity of [Pd{C6H4(CH2N(CH2Ph)2)} (µ-Br)]2 complex as an efficient, stable and non-sensitive to air and moisture catalyst was investigated in the Sonogashira cross-coupling reaction under microwave irradiation. In the presence of catalytic amount of this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene under copper-free conditions. The substituted internal alkynes were produced in excellent yields in short reaction times in NMP at 1...
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An efficient catalytic system using (BeDABCO)2Pd2Cl6 (BeDABCO, benzyl-1,4-diazabicyclo[2.2.2]octane) was developed for the homo-coupling reaction of various aryl halides. Due to the combination of ionic homogeneous metal catalyst and microwave irradiation, symmetric biaryls were produced in excellent yields and short reaction times in N-methyl-2-pyrrolidone at 120 °C. BeDABCO as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species in th...
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Mar 1, 2015·European Journal of Organic Chemistry3.02
#1Toshiyuki Tamura (Chiba University)H-Index: 1
#2Katsuhiko Moriyama (Chiba University)H-Index: 24
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Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes in one pot under metal-cyanide-free conditions.
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Jan 9, 2015·Journal of The Iranian Chemical Society2.02
#1Abdol-Reza Hajipour (IUT: Isfahan University of Technology)H-Index: 21
#2Fatemeh Rafiee (Alzahra University)H-Index: 17
The catalytic activity of dimeric [Pd{C6H2(–CH=NOH)–(OMe)2-2,3}(µ–Cl)]2 complex as an efficient, air, and moisture-tolerant catalyst was investigated in Suzuki cross-coupling reactions of various aryl halides. The combination of homogenous metal catalyst, microwave irradiation, and microwave-active polar solvents gave high yields of substituted biaryl products in short reaction times.
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Nov 1, 2014·Applied Organometallic Chemistry4.11
#1Abdol R. Hajipour (IUT: Isfahan University of Technology)H-Index: 41
#2Fatemeh Dordahan (IUT: Isfahan University of Technology)H-Index: 3
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Nanometric copper oxide supported on silica has been found to be a highly efficient and reusable catalyst for the C–N cross-coupling reaction of amines with aryl halides under ligand-free conditions. Various arylamines with different substituted groups can be synthesized in moderate to good yields. The catalyst can be recycled at least five times without obvious loss in catalytic activity. Copyright © 2014 John Wiley & Sons, Ltd.
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Aug 21, 2014·RSC Advances3.36
#1Wenzhu YinH-Index: 1
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SBA-15 supported Cu2O nanoparticles (Cu2O/SBA-15) have been fabricated and characterized. The as-prepared Cu2O/SBA-15 is a highly effective catalyst for cyanation of aryl iodides using non-toxic K4[Fe(CN)6] as a cyanide source in dimethylformamide (DMF). The approach achieves a high selectivity and an excellent yield without using any ligands and base additives. Moreover, the Cu2O/SBA-15 catalyst shows wide functional group tolerance and reusability with a slight loss of activity.
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