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Volumn 18, Issue 4, 2013, Pages 3712-3724

Microwave assisted suzuki-miyaura and ullmann type homocoupling reactions of 2- and 3-halopyridines using a Pd(OAc)2/benzimidazolium salt and base catalyst system

Author keywords

Homocoupling; Microwave; N heterocyclic carbene; Pyridine derivatives; Suzuki Miyaura reaction

Indexed keywords

ACETIC ACID DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BORONIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM(II) ACETATE; PLATINUM COMPLEX; PYRIDINE DERIVATIVE;

EID: 84876771276     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18043712     Document Type: Article
Times cited : (22)

References (57)
  • 2
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 3
    • 0346786657 scopus 로고    scopus 로고
    • Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998
    • Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998. J. Organomet. Chem. 1999, 576, 147-168.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.1
  • 4
    • 80051736898 scopus 로고    scopus 로고
    • N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: A perfect union
    • Fortman, G.C.; Nolan, S.P. N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. Chem. Soc. Rev. 2011, 40, 5151-5169.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 5151-5169
    • Fortman, G.C.1    Nolan, S.P.2
  • 5
  • 6
    • 0034548738 scopus 로고    scopus 로고
    • Simple and efficient TiCl4-mediated synthesis of biaryls via arylmagnesium compounds
    • Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. Simple and efficient TiCl4-mediated synthesis of biaryls via arylmagnesium compounds. Tetrahedron 2000, 56, 9601-9605.
    • (2000) Tetrahedron , vol.56 , pp. 9601-9605
    • Inoue, A.1    Kitagawa, K.2    Shinokubo, H.3    Oshima, K.4
  • 7
    • 0006789752 scopus 로고
    • Thallium in organic synthesis III. Coupling of aryl and alkyl Grignard reagents
    • McKillop, A.; Elsom, L.F.; Taylor, E.C. Thallium in organic synthesis III. Coupling of aryl and alkyl Grignard reagents. J. Am. Chem. Soc. 1968, 90, 2423-2424.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2423-2424
    • McKillop, A.1    Elsom, L.F.2    Taylor, E.C.3
  • 8
    • 0000924915 scopus 로고    scopus 로고
    • Oxovanadium(V)-induced oxidative coupling of organolithium and -magnesium compounds
    • Ishikawa, T.; Ogawa, A.; Hirao, T. Oxovanadium(V)-induced oxidative coupling of organolithium and -magnesium compounds. Organometallics 1998, 17, 5713-5716.
    • (1998) Organometallics , vol.17 , pp. 5713-5716
    • Ishikawa, T.1    Ogawa, A.2    Hirao, T.3
  • 9
    • 0001166768 scopus 로고
    • Factors determining the course and mechanism of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl Grignard reagents and organic halides
    • Kharasch, M.S.; Fields, E.K. Factors determining the course and mechanism of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl Grignard reagents and organic halides. J. Am. Chem. Soc. 1941, 63, 2316-2320.
    • (1941) J. Am. Chem. Soc. , vol.63 , pp. 2316-2320
    • Kharasch, M.S.1    Fields, E.K.2
  • 10
    • 80051486518 scopus 로고    scopus 로고
    • Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling
    • Nagaki, A.; Uesugi, Y.; Tomida, Y.; Yoshida, J. Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling. Beilstein J. Org. Chem. 2011, 7, 1064-1069.
    • (2011) Beilstein J. Org. Chem. , vol.7 , pp. 1064-1069
    • Nagaki, A.1    Uesugi, Y.2    Tomida, Y.3    Yoshida, J.4
  • 11
    • 84858667548 scopus 로고    scopus 로고
    • Palladium-catalyzed Ullmanntype reductive homocoupling of iodoaryl glycosides
    • Bergeron-Brlek, M.; Giguère, D.; Shiao, T.C.; Saucier, C.; Roy, R. Palladium-catalyzed Ullmanntype reductive homocoupling of iodoaryl glycosides. J. Org. Chem. 2012, 77, 2971-2977.
    • (2012) J. Org. Chem. , vol.77 , pp. 2971-2977
    • Bergeron-Brlek, M.1    Giguère, D.2    Shiao, T.C.3    Saucier, C.4    Roy, R.5
  • 12
    • 0037155532 scopus 로고    scopus 로고
    • Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes
    • Lei, A.W.; Srivastava, M.; Zhang, X.M. Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes. J. Org. Chem. 2002, 67, 1969-1971.
    • (2002) J. Org. Chem. , vol.67 , pp. 1969-1971
    • Lei, A.W.1    Srivastava, M.2    Zhang, X.M.3
  • 13
    • 58649097979 scopus 로고    scopus 로고
    • Very fast Suzuki-Miyaura reaction catalyzed by Pd(OAc)2 under aerobic conditions at room temperature in EGME/H2O
    • Del Zotto, A.; Amoroso, F.; Baratta, W.; Rigo, P. Very fast Suzuki-Miyaura reaction catalyzed by Pd(OAc)2 under aerobic conditions at room temperature in EGME/H2O. Eur. J. Org. Chem. 2009, 1, 110-116.
    • (2009) Eur. J. Org. Chem. , vol.1 , pp. 110-116
    • Del Zotto, A.1    Amoroso, F.2    Baratta, W.3    Rigo, P.4
  • 14
    • 0000180234 scopus 로고    scopus 로고
    • Base and cation effects on the Suzuki cross-coupling of bulky arylboronicacid with halopyridines: Synthesis of pyridylphenols
    • Zhang, H.; Kwong, F.Y.; Tian, Y.; Chan, K.S. Base and cation effects on the Suzuki cross-coupling of bulky arylboronicacid with halopyridines: Synthesis of pyridylphenols. J. Org. Chem. 1998, 63, 6886-6890.
    • (1998) J. Org. Chem. , vol.63 , pp. 6886-6890
    • Zhang, H.1    Kwong, F.Y.2    Tian, Y.3    Chan, K.S.4
  • 15
    • 79960361849 scopus 로고    scopus 로고
    • Investigation of the catalytic activity of a Pd/biphenyl-based phosphine system in the Ullmann homocoupling of aryl bromides
    • Nadri, S.; Azadi, E.; Ataei, A.; Joshaghani, M.; Rafiee, E. Investigation of the catalytic activity of a Pd/biphenyl-based phosphine system in the Ullmann homocoupling of aryl bromides. J. Organomet. Chem. 2011, 696, 2966-2970.
    • (2011) J. Organomet. Chem. , vol.696 , pp. 2966-2970
    • Nadri, S.1    Azadi, E.2    Ataei, A.3    Joshaghani, M.4    Rafiee, E.5
  • 17
    • 33846932758 scopus 로고    scopus 로고
    • A highly efficient catalyst for Suzuki coupling of aryl halides and bromoarylphosphine oxides
    • Joshaghani, M.; Daryanavard, M.; Rafiee, E.; Xiao, J.; Baillie, C. A highly efficient catalyst for Suzuki coupling of aryl halides and bromoarylphosphine oxides. Tetrahedron Lett. 2007, 48, 2025-2027.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2025-2027
    • Joshaghani, M.1    Daryanavard, M.2    Rafiee, E.3    Xiao, J.4    Baillie, C.5
  • 18
    • 84961981202 scopus 로고    scopus 로고
    • Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex
    • Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex. J. Am. Chem. Soc. 2006, 128, 6829-6836.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6829-6836
    • Adamo, C.1    Amatore, C.2    Ciofini, I.3    Jutand, A.4    Lakmini, H.5
  • 19
    • 33746256441 scopus 로고    scopus 로고
    • A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds
    • Billingsley, K.L.; Anderson, K.W.; Buchwald, S.L. A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds. Angew. Chem. Ind. Ed. Engl. 2006, 45, 3484-3488.
    • (2006) Angew. Chem. Ind. Ed. Engl. , vol.45 , pp. 3484-3488
    • Billingsley, K.L.1    Anderson, K.W.2    Buchwald, S.L.3
  • 20
    • 13444282175 scopus 로고    scopus 로고
    • Palladium-catalyzed homocoupling of aryl halides in the presence of floride
    • Seganish, W.M.; Mowery, M.E.; Riggleman, S.; DeShong, P. Palladium-catalyzed homocoupling of aryl halides in the presence of floride. Tetrahedron 2005, 61, 2117-2121.
    • (2005) Tetrahedron , vol.61 , pp. 2117-2121
    • Seganish, W.M.1    Mowery, M.E.2    Riggleman, S.3    Deshong, P.4
  • 21
    • 0034712156 scopus 로고    scopus 로고
    • Simple efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates
    • Wolfe, J.P.; Tomori, H.; Sodighi, J.P.; Yin, J.J.; Buchwald, S.L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem. 2000, 65, 1158-1174.
    • (2000) J. Org. Chem. , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sodighi, J.P.3    Yin, J.J.4    Buchwald, S.L.5
  • 22
    • 45849153837 scopus 로고    scopus 로고
    • Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides
    • Iranpoor, N.; Firouzabadi, H.; Azadi, R. Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides. J. Organomet. Chem. 2008, 693, 2469-2472.
    • (2008) J. Organomet. Chem. , vol.693 , pp. 2469-2472
    • Iranpoor, N.1    Firouzabadi, H.2    Azadi, R.3
  • 23
    • 0000756083 scopus 로고
    • Nickel-Phosphine complex-catalyzed homo coupling of aryl halides in the presence of zinc powder
    • Zembayashi, M.; Tamao, K.; Yoshida, J.; Kumada, M. Nickel-Phosphine complex-catalyzed homo coupling of aryl halides in the presence of zinc powder. Tetrahedron Lett. 1977, 47, 4089-4092.
    • (1977) Tetrahedron Lett. , vol.47 , pp. 4089-4092
    • Zembayashi, M.1    Tamao, K.2    Yoshida, J.3    Kumada, M.4
  • 24
    • 0025328473 scopus 로고
    • Homocoupling of aryl halides using nickel (II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines
    • Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Homocoupling of aryl halides using nickel (II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines. Bull. Chem. Soc. Jpn. 1990, 63, 80-87.
    • (1990) Bull. Chem. Soc. Jpn. , vol.63 , pp. 80-87
    • Iyoda, M.1    Otsuka, H.2    Sato, K.3    Nisato, N.4    Oda, M.5
  • 25
    • 0035924954 scopus 로고    scopus 로고
    • A Pd complex of a tridentate pincer CNC bis-carbene ligand as a robust homogenous Heck catalyst
    • Peris, E.; Loch, J.A.; Mata, J.; Crabtre, R.H. A Pd complex of a tridentate pincer CNC bis-carbene ligand as a robust homogenous Heck catalyst. Chem. Commun. 2001, 2, 201-202.
    • (2001) Chem. Commun. , vol.2 , pp. 201-202
    • Peris, E.1    Loch, J.A.2    Mata, J.3    Crabtre, R.H.4
  • 26
    • 34547777869 scopus 로고    scopus 로고
    • Microwave-assisted Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of aryl chlorides and bromides in water using stable benzothiazole-based palladium(II) precatalysts
    • Dawood, K.M. Microwave-assisted Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of aryl chlorides and bromides in water using stable benzothiazole-based palladium(II) precatalysts. Tetrahedron 2007, 63, 9642-9651.
    • (2007) Tetrahedron , vol.63 , pp. 9642-9651
    • Dawood . K, M.1
  • 27
    • 34447097175 scopus 로고    scopus 로고
    • Microwave-assisted synthesis in water as solvent
    • Dallinger, D.; Kappe, C.O. Microwave-assisted synthesis in water as solvent. Chem. Rev. 2007, 107, 2563-2591.
    • (2007) Chem. Rev. , vol.107 , pp. 2563-2591
    • Dallinger, D.1    Kappe, C.O.2
  • 28
    • 70350518831 scopus 로고    scopus 로고
    • Microwave-assisted Cross-Coupling and hydrogenation chemistry by using heterogeneous transition-metal catalysts: An evaluation of the role of selective catalyst heating
    • Irfan, M.; Fuchs, M.; Glasnov, T.N.; Kappe, C.O. Microwave-assisted Cross-Coupling and hydrogenation chemistry by using heterogeneous transition-metal catalysts: An evaluation of the role of selective catalyst heating. Chem. Eur. J. 2009, 15, 11608-11618.
    • (2009) Chem. Eur. J. , vol.15 , pp. 11608-11618
    • Irfan, M.1    Fuchs, M.2    Glasnov, T.N.3    Kappe, C.O.4
  • 29
    • 78649335011 scopus 로고    scopus 로고
    • Studies of microwaveenhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate
    • Brooker, M.D.; Cooper, S.M., Jr.; Hodges, D.R.; Carter, R.R.; Wyatt, J.K. Studies of microwaveenhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate. Tetrahedron Lett. 2010, 51, 6748-6752.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 6748-6752
    • Brooker, M.D.1    Cooper Jr., S.M.2    Hodges, D.R.3    Carter, R.R.4    Wyatt, J.K.5
  • 30
    • 78650679976 scopus 로고    scopus 로고
    • Microwave-assisted Suzuki reaction catalyzed by Pd(0)-PVP nanoparticles
    • Martins, D.L.; Alvarez, H.M.; Aguiar, L.C.S. Microwave-assisted Suzuki reaction catalyzed by Pd(0)-PVP nanoparticles. Tetrahedron Lett. 2010, 51, 6814-6817.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 6814-6817
    • Martins, D.L.1    Alvarez, H.M.2    Aguiar, L.C.S.3
  • 31
    • 79960838340 scopus 로고    scopus 로고
    • A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane under conventional and microwave irradiation conditions
    • Hajipour, A.R.; Karami, K.; Tavakoli, G. A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane under conventional and microwave irradiation conditions. Appl. Organometal. Chem. 2011, 25, 567-576.
    • (2011) Appl. Organometal. Chem. , vol.25 , pp. 567-576
    • Hajipour, A.R.1    Karami, K.2    Tavakoli, G.3
  • 32
    • 84857550615 scopus 로고    scopus 로고
    • Microwave-assisted Ullmann-type coupling reactions in alkaline water
    • Gädda, T.M.; Kawanishi, Y.; Miyazawa, A. Microwave-assisted Ullmann-type coupling reactions in alkaline water. Synth. Commun. 2012, 42, 1259-1267.
    • (2012) Synth. Commun. , vol.42 , pp. 1259-1267
    • Gädda, T.M.1    Kawanishi, Y.2    Miyazawa, A.3
  • 33
    • 66149168828 scopus 로고    scopus 로고
    • Elimination of an alkyl group from imidazolium salts: Imidazolecoordinated dinuclear monodentate NHC-palladium complexes driven by self-assembly and their application in the Heck reaction
    • Liu, L.-J.; Wang, F.; Shi, M. Elimination of an alkyl group from imidazolium salts: Imidazolecoordinated dinuclear monodentate NHC-palladium complexes driven by self-assembly and their application in the Heck reaction. Eur. J. Inorg. Chem. 2009, 13, 1723-1728.
    • (2009) Eur. J. Inorg. Chem. , vol.13 , pp. 1723-1728
    • Liu, L.-J.1    Wang, F.2    Shi, M.3
  • 34
    • 77950921650 scopus 로고    scopus 로고
    • Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions
    • Yilmaz, Ü.; Şireci, N.; Deniz, S.; Küçükbay, H. Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions. Appl. Organometal. Chem. 2010, 24, 414-420.
    • (2010) Appl. Organometal. Chem. , vol.24 , pp. 414-420
    • Yilmaz, Ü.1    Şireci, N.2    Deniz, S.3    Küçükbay, H.4
  • 35
    • 79955047652 scopus 로고    scopus 로고
    • Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group
    • Yilmaz, Ü.; Küçükbay, H.; Şireci, N.; Akkurt, M.; Günal, S.; Durmaz, R.; Tahir, M.N. Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group. Appl. Organometal. Chem. 2011, 25, 366-373.
    • (2011) Appl. Organometal. Chem. , vol.25 , pp. 366-373
    • Yilmaz, Ü.1    Küçükbay, H.2    Şireci, N.3    Akkurt, M.4    Günal, S.5    Durmaz, R.6    Tahir, M.N.7
  • 36
    • 79953040800 scopus 로고    scopus 로고
    • Synthesis, characterization and microwave-assisted catalytic activity of novel benzimidazole salts bearing piperidine and morpholine moieties in Heck cross-coupling reactions
    • Küçükbay, H.; Şireci, N.; Yilmaz, Ü.; Akkurt, M.; Yalçin, Ş.P.; Tahir, M.N.; Ott, H. Synthesis, characterization and microwave-assisted catalytic activity of novel benzimidazole salts bearing piperidine and morpholine moieties in Heck cross-coupling reactions. Appl. Organometal. Chem. 2011, 25, 255-261.
    • (2011) Appl. Organometal. Chem. , vol.25 , pp. 255-261
    • Küçükbay, H.1    Şireci, N.2    Yilmaz, Ü.3    Akkurt, M.4    Yalçin, Ş.P.5    Tahir, M.N.6    Ott, H.7
  • 37
    • 84858812011 scopus 로고    scopus 로고
    • Synthesis, characterization, and microwave-promoted catalytic activity of novel benzimidazole salts bearing silicon-containing substituents in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under aerobic conditions
    • Küçükbay, H.; Şireci, N.; Yilmaz, Ü.; Deniz, S.; Akkurt, M.; Baktir, Z.; Büyükgüngör, O. Synthesis, characterization, and microwave-promoted catalytic activity of novel benzimidazole salts bearing silicon-containing substituents in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Turk. J. Chem. 2012, 36, 201-217.
    • (2012) Turk. J. Chem. , vol.36 , pp. 201-217
    • Küçükbay, H.1    Şireci, N.2    Yilmaz, Ü.3    Deniz, S.4    Akkurt, M.5    Baktir, Z.6    Büyükgüngör, O.7
  • 38
    • 77956310534 scopus 로고    scopus 로고
    • Microwave assisted catalytic activity of some bis-5(6)- nitrobenzimidazole salts for Heck and Suzuki cross-coupling reactions
    • Şireci, N.; Yilmaz, Ü.; Küçükbay, H. Microwave assisted catalytic activity of some bis-5(6)- nitrobenzimidazole salts for Heck and Suzuki cross-coupling reactions. Asian J. Chem. 2010, 22, 7153-7158.
    • (2010) Asian J. Chem. , vol.22 , pp. 7153-7158
    • Şireci, N.1    Yilmaz, Ü.2    Küçükbay, H.3
  • 39
    • 84875628466 scopus 로고    scopus 로고
    • Synthesis, characterization and microwavepromoted catalytic activity of novel N-phenylbenzimidazolium salts in Heck-Mizoroki and Suzuki- Miyaura cross-coupling reactions under mild condtiyions
    • Yilmaz, Ü.; Küçükbay, H.; Deniz, S.; Şireci, N. Synthesis, characterization and microwavepromoted catalytic activity of novel N-phenylbenzimidazolium salts in Heck-Mizoroki and Suzuki- Miyaura cross-coupling reactions under mild condtiyions. Molecules, 2013, 18, 2501-2517.
    • (2013) Molecules , vol.18 , pp. 2501-2517
    • Yilmaz, Ü.1    Küçükbay, H.2    Deniz, S.3    Şireci, N.4
  • 40
    • 84864441484 scopus 로고    scopus 로고
    • Palladium-catalysed direct arylation of heteroaromatics with functionalised bromopyridines
    • Bensaid, S.; Doucet, H. Palladium-catalysed direct arylation of heteroaromatics with functionalised bromopyridines. Tetrahedron 2012, 68, 7655-7662.
    • (2012) Tetrahedron , vol.68 , pp. 7655-7662
    • Bensaid, S.1    Doucet, H.2
  • 41
    • 70349915668 scopus 로고    scopus 로고
    • A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media
    • Liu, C.; Yang, W. A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media. Chem. Commun. 2009, 41, 6267-6269.
    • (2009) Chem. Commun. , vol.41 , pp. 6267-6269
    • Liu, C.1    Yang, W.2
  • 42
    • 67649863778 scopus 로고    scopus 로고
    • Amidinate-ligated iridium(III) bis(2- pyridyl)phenyl complex as an excellent phosphorescent material for electroluminescence devices
    • Liu, Y.; Ye, K.; Fan, Y.; Song, W.; Wang, Y.; Hou, Z. Amidinate-ligated iridium(III) bis(2- pyridyl)phenyl complex as an excellent phosphorescent material for electroluminescence devices. Chem. Commun. 2009, 3699-3701.
    • (2009) Chem. Commun. , pp. 3699-3701
    • Liu, Y.1    Ye, K.2    Fan, Y.3    Song, W.4    Wang, Y.5    Hou, Z.6
  • 43
    • 0034286415 scopus 로고    scopus 로고
    • Regiospecific cross-coupling of haloaryls and pyridine to 2-phenylpyridine using water, zinc, and catalytic palladium on carbon
    • Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D.E.; Sasson, Y. Regiospecific cross-coupling of haloaryls and pyridine to 2-phenylpyridine using water, zinc, and catalytic palladium on carbon. J. Chem. Soc. Perkin Trans. 2 2000, 9, 1809-1812.
    • (2000) J. Chem. Soc. Perkin Trans. 2 , vol.9 , pp. 1809-1812
    • Mukhopadhyay, S.1    Rothenberg, G.2    Gitis, D.3    Baidossi, M.4    Ponde, D.E.5    Sasson, Y.6
  • 44
    • 0344391956 scopus 로고    scopus 로고
    • Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines
    • Tagata, T.; Nishida, M. Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines. J. Org. Chem. 2003, 68, 9412-9415.
    • (2003) J. Org. Chem. , vol.68 , pp. 9412-9415
    • Tagata, T.1    Nishida, M.2
  • 45
    • 33745721269 scopus 로고    scopus 로고
    • A versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles
    • Kudo, N.; Perseghini, M.; Fu, G.C. A versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles. Angew. Chem. Ind. Ed. Engl. 2006, 45, 1282-1284.
    • (2006) Angew. Chem. Ind. Ed. Engl. , vol.45 , pp. 1282-1284
    • Kudo, N.1    Perseghini, M.2    Fu, G.C.3
  • 46
    • 77953575860 scopus 로고    scopus 로고
    • Iron-mediated direct Suzuki-Miyaura reaction: A new method for the ortho-arylation of pyrrole and pyridine
    • Wen, J.; Qin, S.; Ma, L.-F.; Dong, L.; Zhang, J.; Liu, S.-S.; Duan, Y.-S.; Chen, S.-Y.; Hu, C.-W.; Yu, X.-Q. Iron-Mediated Direct Suzuki-Miyaura Reaction: A New Method for the ortho-Arylation of Pyrrole and Pyridine. Org. Lett. 2010, 12, 2694-2697.
    • (2010) Org. Lett. , vol.12 , pp. 2694-2697
    • Wen, J.1    Qin, S.2    Ma, L.-F.3    Dong, L.4    Zhang, J.5    Liu, S.-S.6    Duan, Y.-S.7    Chen, S.-Y.8    Hu, C.-W.9    Yu, X.-Q.10
  • 47
    • 0000658001 scopus 로고    scopus 로고
    • Palladium-catalyzed (Ullmann-Type) homocoupling of aryl halides: A convenient and general synthesis of symmetrical biaryls via inter- and intramolecular coupling reactions
    • Hennings, D.D.; Iwama, T.; Rawal, V.H. Palladium-catalyzed (Ullmann-Type) homocoupling of aryl halides: A convenient and general synthesis of symmetrical biaryls via inter- and intramolecular coupling reactions. Org. Lett. 1999, 1, 1205-1208.
    • (1999) Org. Lett. , vol.1 , pp. 1205-1208
    • Hennings, D.D.1    Iwama, T.2    Rawal, V.H.3
  • 48
    • 0037155503 scopus 로고    scopus 로고
    • Electrochemical homocoupling of 2-bromomethylpyridines catalyzed by nickel complexes
    • França, K.W.R.; Navarro, M.; Leonel, E.; Durandetti, M.; Nedelec, J.-Y. Electrochemical homocoupling of 2-bromomethylpyridines catalyzed by nickel complexes. J. Org. Chem. 2002, 67, 1838-1842.
    • (2002) J. Org. Chem. , vol.67 , pp. 1838-1842
    • França, K.W.R.1    Navarro, M.2    Leonel, E.3    Durandetti, M.4    Nedelec, J.-Y.5
  • 50
    • 33747703733 scopus 로고    scopus 로고
    • Homocoupling of aryl bromides catalyzed by nickel chloride in pyridine
    • Tao, X.; Zhou, W.; Zhang, Y.; Dai, C.; Shen, D.; Huang, M. Homocoupling of aryl bromides catalyzed by nickel chloride in pyridine. Chin. J. Chem. 2006, 24, 939-942.
    • (2006) Chin. J. Chem. , vol.24 , pp. 939-942
    • Tao, X.1    Zhou, W.2    Zhang, Y.3    Dai, C.4    Shen, D.5    Huang, M.6
  • 51
    • 79960847587 scopus 로고    scopus 로고
    • Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides
    • Park, B.R.; Kim, K.H.; Kim, T.H.; Kim, J.N. Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides. Tetrahedron Lett. 2011, 52, 4405-4407.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 4405-4407
    • Park, B.R.1    Kim, K.H.2    Kim, T.H.3    Kim, J.N.4
  • 52
    • 52049087157 scopus 로고    scopus 로고
    • A heterogeneous-catalyst-based, microwave-assisted protocol for the synthesis of 2,2'-bipyridines
    • Moore, L.R.; Vicic, D.A. A heterogeneous-catalyst-based, microwave-assisted protocol for the synthesis of 2,2'-bipyridines. Chem. Asian. J. 2008, 3, 1046-1049.
    • (2008) Chem. Asian. J. , vol.3 , pp. 1046-1049
    • Moore, L.R.1    Vicic, D.A.2
  • 53
    • 72449210312 scopus 로고    scopus 로고
    • Synthesis of novel synthetic intermediates from the reaction of benzimidazole and triazole carbenes with ketenimines and their application in the construction of spiro-pyrroles
    • Mo, J.-M.; Ma, Y.-G.; Cheng, Y. Synthesis of novel synthetic intermediates from the reaction of benzimidazole and triazole carbenes with ketenimines and their application in the construction of spiro-pyrroles. Org. Biomol. Chem. 2009, 7, 5010-5019.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 5010-5019
    • Mo, J.-M.1    Ma, Y.-G.2    Cheng, Y.3
  • 55
    • 32644469675 scopus 로고    scopus 로고
    • The application of organic bases in microwave-promoted Suzuki coupling reactions in water
    • Chanthavong, F.; Leadbeater, N.E. The application of organic bases in microwave-promoted Suzuki coupling reactions in water. Tetrahedron Lett. 2006, 47, 1909-1912.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 1909-1912
    • Chanthavong, F.1    Leadbeater, N.E.2
  • 56
    • 20044396990 scopus 로고    scopus 로고
    • A facile and efficient synthesis of N,N-dimethylarylamines from aryl bromides Chin
    • Zhao, J.K.; Wang, Y.G. A facile and efficient synthesis of N,N-dimethylarylamines from aryl bromides Chin. Chem. Lett. 2002, 13, 1149-1151.
    • (2002) Chem. Lett. , vol.13 , pp. 1149-1151
    • Zhao, J.K.1    Wang, Y.G.2
  • 57
    • 84867728644 scopus 로고    scopus 로고
    • N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed Amination between Aryl Chlorides and Amides
    • Chen, W.-X.; Shao, L.-X. N-Heterocyclic Carbene-Palladium(II)-1- Methylimidazole Complex Catalyzed Amination between Aryl Chlorides and Amides. J. Org. Chem. 2012, 77, 9236-9239.
    • (2012) J. Org. Chem. , vol.77 , pp. 9236-9239
    • Chen, W.-X.1    Shao, L.-X.2


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