메뉴 건너뛰기




Volumn 17, Issue 11, 2012, Pages 12506-12520

Aqueous synthesis of 1-H-2-substituted benzimidazoles via transition-metal-free intramolecular amination of aryl iodides

Author keywords

Aqueous synthesis; Aryl iodides; Benzimidazoles; N arylation; Transition metal free conditions

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; CARBONIC ACID DERIVATIVE; IODIDE; POTASSIUM; POTASSIUM CARBONATE; SOLVENT; TRANSITION ELEMENT; WATER;

EID: 84870156616     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171112506     Document Type: Article
Times cited : (41)

References (69)
  • 1
    • 33750525295 scopus 로고    scopus 로고
    • Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing -CONH- Bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms
    • Desai, K.G.; Desai, K.R. Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing -CONH- bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorg. Med. Chem. 2006, 14, 8271-8279.
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 8271-8279
    • Desai, K.G.1    Desai, K.R.2
  • 2
    • 33947728884 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers
    • Güven, Ö.Ö.; Erdoǧan, T.; Göker, H.; Ylidiz, S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg. Med. Chem. Lett. 2007, 17, 2233-2236.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 2233-2236
    • Güven, O.O.1    Erdoǧan, T.2    Göker, H.3    Ylidiz, S.4
  • 4
    • 33845351607 scopus 로고    scopus 로고
    • Antihelminthic activity of some newly synthesized 5(6)-(un)substituted- 1H-benzimidazol-2-ylthioacetylpiperazine derivatives
    • Mavrova, A.T.; Anichina, K.K.; Vuchev, D.I.; Tsenov, J.A.; Denkova, P.S.; Kondeva, M.S.; Micheva, M.K. Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives. Eur. J. Med. Chem. 2006, 41, 1412-1420.
    • (2006) Eur. J. Med. Chem. , vol.41 , pp. 1412-1420
    • Mavrova, A.T.1    Anichina, K.K.2    Vuchev, D.I.3    Tsenov, J.A.4    Denkova, P.S.5    Kondeva, M.S.6    Micheva, M.K.7
  • 8
    • 0034489297 scopus 로고    scopus 로고
    • Design, synthesis and antitumor cytotoxicity of novel bis-benzimidazoles
    • Singh, A.K.; Lown, J.W. Design, synthesis and antitumor cytotoxicity of novel bis-benzimidazoles. Anticancer Drug Des. 2000, 15, 265-275.
    • (2000) Anticancer Drug Des. , vol.15 , pp. 265-275
    • Singh, A.K.1    Lown, J.W.2
  • 9
    • 84961983597 scopus 로고    scopus 로고
    • An experimental and computational analysis on the differential role of the positional isomers of symmetric bis-2-(pyridyl)-1H-benzimidazoles as DNA binding agents
    • Chaudhuri, P.; Ganguly, B.; Bhattacharya, S. An Experimental and Computational Analysis on the Differential Role of the Positional Isomers of Symmetric Bis-2-(pyridyl)-1H-benzimidazoles as DNA Binding Agents. J. Org. Chem. 2007, 72, 1912-1923.
    • (2007) J. Org. Chem. , vol.72 , pp. 1912-1923
    • Chaudhuri, P.1    Ganguly, B.2    Bhattacharya, S.3
  • 10
    • 50949127251 scopus 로고    scopus 로고
    • Synthesis, reactivity and biological activity of benzimidazoles
    • Khan, M.T.H., Ed.; Springer: Berlin, Germany
    • Alamgir, M.; Black, D.St.C.; Kumar, N. Synthesis, Reactivity and Biological Activity of Benzimidazoles. In Topics in Heterocyclic Chemistry; Khan, M.T.H., Ed.; Springer: Berlin, Germany, 2007; Volume 9, pp. 87-118.
    • (2007) Topics in Heterocyclic Chemistry , vol.9 , pp. 87-118
    • Alamgir, M.1    Black, D.St.C.2    Kumar, N.3
  • 11
    • 33947716471 scopus 로고    scopus 로고
    • Benzene benzimidazole containing pd(II) metallacycle: Synthesis, X-ray crystallographic characterization and its use as an efficient suzuki coupling catalyst
    • Pal, S.; Hwang, W.-S.; Lin, I.J.B.; Lee, C.-S. Benzene benzimidazole containing Pd(II) metallacycle: Synthesis, X-ray crystallographic characterization and its use as an efficient Suzuki coupling catalyst. J. Mol. Catal. A: Chem. 2007, 269, 197-203.
    • (2007) J. Mol. Catal. A: Chem. , vol.269 , pp. 197-203
    • Pal, S.1    Hwang, W.-S.2    Lin, I.J.B.3    Lee, C.-S.4
  • 12
    • 34248370196 scopus 로고    scopus 로고
    • Synthesis, characterization and ethylene oligomerization studies of nickel complexes bearing 2-benzimidazolylpyridine derivatives
    • Hao, P.; Zhang, S.; Sun, W.-H.; Shi, Q.; Adewuyi, S.; Lu, X.; Li, P. Synthesis, Characterization and Ethylene Oligomerization Studies of Nickel Complexes Bearing 2-Benzimidazolylpyridine Derivatives. Organometallics 2007, 26, 2439-2446.
    • (2007) Organometallics , vol.26 , pp. 2439-2446
    • Hao, P.1    Zhang, S.2    Sun, W.-H.3    Shi, Q.4    Adewuyi, S.5    Lu, X.6    Li, P.7
  • 13
    • 0022754373 scopus 로고
    • Synthesis of pyrazolo[4′,3′:5,6]pyrido[1,2-a]benzimidazole derivatives and study of their fluorescence properties
    • Rajadhyaksha, D.D.; Rangnekar, D.W. Synthesis of pyrazolo[4′, 3′:5,6]pyrido[1,2-a]benzimidazole derivatives and study of their fluorescence properties. J. Chem. Technol. Biotechnol. 1986, 36, 300-304.
    • (1986) J. Chem. Technol. Biotechnol. , vol.36 , pp. 300-304
    • Rajadhyaksha, D.D.1    Rangnekar, D.W.2
  • 14
    • 24344468306 scopus 로고    scopus 로고
    • Recent developments on proton conduc-ting poly(2,5-benzimidazole) (ABPBI) membranes for high temperature poly-mer electrolyte membrane fuel cells
    • Asensio, J.A.; Gomez-Romero, P. Recent Developments on Proton Conduc-ting Poly(2,5-benzimidazole) (ABPBI) Membranes for High Temperature Poly-mer Electrolyte Membrane Fuel Cells. Fuel Cells 2005, 5, 336-343.
    • (2005) Fuel Cells , vol.5 , pp. 336-343
    • Asensio, J.A.1    Gomez-Romero, P.2
  • 15
    • 33747821670 scopus 로고    scopus 로고
    • Highly efficient white organic light emitting diodes comprising an interlayer to separate fluorescent and phosphorescent regions
    • doi:10.1063/1.2338588
    • Schwartz, G.; Fehse, K.; Pfeiffer, M.; Walzer, K.; Leo, K. Highly efficient white organic light emitting diodes comprising an interlayer to separate fluorescent and phosphorescent regions. Appl. Phys. Lett. 2006, 89, doi:10.1063/1.2338588.
    • (2006) Appl. Phys. Lett. , vol.89
    • Schwartz, G.1    Fehse, K.2    Pfeiffer, M.3    Walzer, K.4    Leo, K.5
  • 16
    • 80054902396 scopus 로고    scopus 로고
    • Developments towards regioselective synthesis of 1,2-disubstituted benzimidazoles
    • Carvalho, L.C.R.; Fernandes, E.; Marques, M.M.B. Developments Towards Regioselective Synthesis of 1,2-Disubstituted Benzimidazoles. Chem. Eur. J. 2011, 17, 12544-12555.
    • (2011) Chem. Eur. J. , vol.17 , pp. 12544-12555
    • Carvalho, L.C.R.1    Fernandes, E.2    Marques, M.M.B.3
  • 17
    • 84870193358 scopus 로고    scopus 로고
    • Ring syntheses involving formation of two bonds: [4+1] fragments
    • Meth-Cohn, O., Ed.; Academic: London, UK
    • Grimmett, M.R. Ring Syntheses Involving Formation of Two Bonds: [4+1] Fragments. In Imidazole and Benzimidazole Synthesis; Meth-Cohn, O., Ed.; Academic: London, UK, 1997; pp. 63-102.
    • (1997) Imidazole and Benzimidazole Synthesis , pp. 63-102
    • Grimmett, M.R.1
  • 18
    • 12344311063 scopus 로고    scopus 로고
    • A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization
    • Yang, D.; Fokas, D.; Li, J.; Yu, L.; Baldino, C.M. A Versatile Method for the Synthesis of Benzimidazoles from o-Nitroanilines and Aldehydes in One Step via a Reductive Cyclization. Synthesis 2005, 47-56.
    • Synthesis , vol.2005 , pp. 47-56
    • Yang, D.1    Fokas, D.2    Li, J.3    Yu, L.4    Baldino, C.M.5
  • 19
    • 51549105076 scopus 로고    scopus 로고
    • Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
    • Bahrami, K.; Khodaei, M.M.; Naali, F. Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles. J. Org. Chem. 2008, 73, 6835-6837.
    • (2008) J. Org. Chem. , vol.73 , pp. 6835-6837
    • Bahrami, K.1    Khodaei, M.M.2    Naali, F.3
  • 20
    • 55249099550 scopus 로고    scopus 로고
    • Concise synthesis of telmisartan via decarboxylative cross-coupling
    • Goossen, L.J.; Knauber, T. Concise Synthesis of Telmisartan via Decarboxylative Cross-Coupling. J. Org. Chem. 2008, 73, 8631-8634.
    • (2008) J. Org. Chem. , vol.73 , pp. 8631-8634
    • Goossen, L.J.1    Knauber, T.2
  • 21
    • 0037017716 scopus 로고    scopus 로고
    • An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles
    • Brain, C.T.; Brunton, S.A. An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles. Tetrahedron Lett. 2002, 43, 1893-1895.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1893-1895
    • Brain, C.T.1    Brunton, S.A.2
  • 22
    • 0043009828 scopus 로고    scopus 로고
    • An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry
    • Brain, C.T.; Brunton, S.A. An Improved Procedure for the Synthesis of Benzimidazoles, Using Palladium-Catalyzed Aryl-Amination Chemistry. J. Org. Chem. 2003, 68, 6814-6816.
    • (2003) J. Org. Chem. , vol.68 , pp. 6814-6816
    • Brain, C.T.1    Brunton, S.A.2
  • 23
    • 84055178178 scopus 로고    scopus 로고
    • Regiospecific synthesis of 1,2-disubstituted (Hetero)aryl fused imidazoles with tunable fluorescent emission
    • Zhao, D.; Hu, J.; Wu, N.; Huang, X.; Qin, X.; Lan, J.; You, J. Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission. Org. Lett. 2011, 13, 6516-6519.
    • (2011) Org. Lett. , vol.13 , pp. 6516-6519
    • Zhao, D.1    Hu, J.2    Wu, N.3    Huang, X.4    Qin, X.5    Lan, J.6    You, J.7
  • 25
    • 53349123998 scopus 로고    scopus 로고
    • A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles
    • Zheng, N.; Anderson, K.W.; Huang, X.H.; Nguyen, H.N.; Buchwald, S.L. A Palladium-Catalyzed Regiospecific Synthesis of N-Aryl Benzimidazoles. Angew. Chem. 2007, 119, 7653-7656;
    • (2007) Angew. Chem. , vol.119 , pp. 7653-7656
    • Zheng, N.1    Anderson, K.W.2    Huang, X.H.3    Nguyen, H.N.4    Buchwald, S.L.5
  • 27
    • 0038003832 scopus 로고    scopus 로고
    • Copper- and palladium-catalyzed intramolecular aryl guanidinylation: An efficient method for the synthesis of 2-aminobenzimidazoles
    • Evindar, G.; Batey, R.A. Copper- and Palladium-Catalyzed Intramolecular Aryl Guanidinylation: An Efficient Method for the Synthesis of 2-Aminobenzimidazoles. Org. Lett. 2003, 5, 133-136.
    • (2003) Org. Lett. , vol.5 , pp. 133-136
    • Evindar, G.1    Batey, R.A.2
  • 28
    • 18844423518 scopus 로고    scopus 로고
    • Synthesis of purines and other fused imidazoles from acyclic amidines and guanidines
    • Szczepankiewicz, B.G.; Rohde, J.J.; Kurukulasuriyz, R. Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines. Org. Lett. 2005, 7, 1833-1835.
    • (2005) Org. Lett. , vol.7 , pp. 1833-1835
    • Szczepankiewicz, B.G.1    Rohde, J.J.2    Kurukulasuriyz, R.3
  • 29
    • 78651504130 scopus 로고    scopus 로고
    • Copper-catalyzed intramolecular C-N bond formation: A straightforward synthesis of benzimidazole derivatives in water
    • Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. Copper-Catalyzed Intramolecular C-N Bond Formation: A Straightforward Synthesis of Benzimidazole Derivatives in Water. J. Org. Chem. 2011, 76, 716-719.
    • (2011) J. Org. Chem. , vol.76 , pp. 716-719
    • Peng, J.1    Ye, M.2    Zong, C.3    Hu, F.4    Feng, L.5    Wang, X.6    Wang, Y.7    Chen, C.8
  • 30
    • 53349151195 scopus 로고    scopus 로고
    • C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    • Brasche, G.; Buchwald, S.L. C-H Functionalization/C-N Bond Formation: Copper-Catalyzed Synthesis of Benzimidazoles from Amidines. Angew. Chem. 2008, 120, 1958-1960;
    • (2008) Angew. Chem. , vol.120 , pp. 1958-1960
    • Brasche, G.1    Buchwald, S.L.2
  • 32
    • 53549120107 scopus 로고    scopus 로고
    • Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process
    • Zou, B.L.; Yuan, Q.L.; Ma, D.-W. Synthesis of 1,2-Disubstituted Benzimidazoles by a Cu-Catalyzed Cascade Aryl Amination/Condensation Process. Angew. Chem. 2007, 119, 2652-2655;
    • (2007) Angew. Chem. , vol.119 , pp. 2652-2655
    • Zou, B.L.1    Yuan, Q.L.2    Ma, D.-W.3
  • 34
    • 82255170708 scopus 로고    scopus 로고
    • Copper-catalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C-N bond formation
    • Kim, Y.; Kumar, M.R.; Park, N.; Heo, Y.; Lee, S. Copper-Catalyzed, One-Pot, Three-Component Synthesis of Benzimidazoles by Condensation and C-N Bond Formation. J. Org. Chem. 2011, 76, 9577-9583.
    • (2011) J. Org. Chem. , vol.76 , pp. 9577-9583
    • Kim, Y.1    Kumar, M.R.2    Park, N.3    Heo, Y.4    Lee, S.5
  • 35
    • 74949105836 scopus 로고    scopus 로고
    • Reactivity-controlled regioselectivity: A regiospecific synthesis of 1,2-disubstituted benzimidazoles
    • Deng, X.; Mani, N.S. Reactivity-Controlled Regioselectivity: A Regiospecific Synthesis of 1,2-Disubstituted Benzimidazoles. Eur. J. Org. Chem. 2010, 680-686.
    • Eur. J. Org. Chem. , vol.2010 , pp. 680-686
    • Deng, X.1    Mani, N.S.2
  • 36
    • 68049083708 scopus 로고    scopus 로고
    • CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles
    • Deng, X.; McAllister, H.; Mani, N.S. CuI-Catalyzed Amination of Arylhalides with Guanidines or Amidines: A Facile Synthesis of 1-H-2-Substituted Benzimidazoles. J. Org. Chem. 2009, 74, 5742-5745.
    • (2009) J. Org. Chem. , vol.74 , pp. 5742-5745
    • Deng, X.1    McAllister, H.2    Mani, N.S.3
  • 37
    • 0141853186 scopus 로고    scopus 로고
    • Efficient nickel-mediated intramolecular amination of aryl chlorides
    • Amrani, R.O.; Thomas, A.; Brenner, E.; Schneider, R.; Fort, Y. Efficient Nickel-Mediated Intramolecular Amination of Aryl Chlorides. Org. Lett. 2003, 5, 2311-2314.
    • (2003) Org. Lett. , vol.5 , pp. 2311-2314
    • Amrani, R.O.1    Thomas, A.2    Brenner, E.3    Schneider, R.4    Fort, Y.5
  • 38
    • 49649102647 scopus 로고    scopus 로고
    • Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides
    • Shen, M.; Driver, T.G. Iron(II) Bromide-Catalyzed Synthesis of Benzimidazoles from Aryl Azides. Org. Lett. 2008, 10, 3367-3370.
    • (2008) Org. Lett. , vol.10 , pp. 3367-3370
    • Shen, M.1    Driver, T.G.2
  • 39
    • 78649510172 scopus 로고    scopus 로고
    • Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: Synthesis of benzimidazoles and benzoxazoles
    • Saha, P.; Ali, M.A.; Ghosh, P.; Punniyamurthy, T. Cobalt-catalyzed intramolecular C-N and C-O cross-coupling reactions: Synthesis of benzimidazoles and benzoxazoles. Org. Biomol. Chem. 2010, 8, 5692-5699.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 5692-5699
    • Saha, P.1    Ali, M.A.2    Ghosh, P.3    Punniyamurthy, T.4
  • 41
    • 0010557399 scopus 로고
    • Nucleophilic displacement reactions in aromatic systems. IV. Rates of reaction of 1-halo-2,4-dinitrobenzene with N-butylamine in chloroform and with N-butylamine and t-butylamine in dimethylformamide
    • Ross, S.D. Nucleophilic Displacement Reactions in Aromatic Systems. IV. Rates of Reaction of 1-Halo-2,4-dinitrobenzene with N-Butylamine in Chloroform and with N-Butylamine and t-Butylamine in Dimethylformamide. J. Am. Chem. Soc. 1959, 81, 2113-2115.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 2113-2115
    • Ross, S.D.1
  • 42
    • 0035936728 scopus 로고    scopus 로고
    • Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides
    • Beller, M.; Breindl, C.; Riermeier, R.H.; Tillack, A. Synthesis of 2,3-Dihydroindoles, Indoles, and Anilines by Transition Metal-Free Amination of Aryl Chlorides. J. Org. Chem. 2001, 66, 1403-1412.
    • (2001) J. Org. Chem. , vol.66 , pp. 1403-1412
    • Beller, M.1    Breindl, C.2    Riermeier, R.H.3    Tillack, A.4
  • 43
    • 0345255658 scopus 로고    scopus 로고
    • Rapid and efficient microwave-assisted amination of electron-rich aryl halides without a transition-metal catalyst
    • Shi, L.; Wang, M.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.-Q. Rapid and Efficient Microwave-Assisted Amination of Electron-Rich Aryl Halides without a Transition-Metal Catalyst. Org. Lett. 2003, 5, 3515-3517.
    • (2003) Org. Lett. , vol.5 , pp. 3515-3517
    • Shi, L.1    Wang, M.2    Fan, C.-A.3    Zhang, F.-M.4    Tu, Y.-Q.5
  • 44
    • 4143053592 scopus 로고    scopus 로고
    • 2O in amination reactions via direct coupling of aryl halides and sec-alicyclic amines
    • 2O in Amination Reactions via Direct Coupling of Aryl Halides and sec-Alicyclic Amines. Synlett 2004, 1747-1750.
    • Synlett , vol.2004 , pp. 1747-1750
    • Varala, R.1    Ramu, E.2    Alam, M.M.3    Adapa, S.R.4
  • 45
    • 58149149619 scopus 로고    scopus 로고
    • Transition metal-free amination of aryl halides - A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines
    • Bolliger, J.L.; Frech, C.M. Transition metal-free amination of aryl halides - A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines. Tetrahedron 2009, 65, 1180-1187.
    • (2009) Tetrahedron , vol.65 , pp. 1180-1187
    • Bolliger, J.L.1    Frech, C.M.2
  • 46
    • 77952398665 scopus 로고    scopus 로고
    • Metal-free coupling of azoles with 2- and 3-haloindoles providing access to novel 2- or 3-(Azol-1-yl)indole derivatives
    • Poirier, M.; Goudreau, S.; Poulin, J.; Savole, J.; Beaulieu, P.L. Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives. Org. Lett. 2010, 12, 2334-2337.
    • (2010) Org. Lett. , vol.12 , pp. 2334-2337
    • Poirier, M.1    Goudreau, S.2    Poulin, J.3    Savole, J.4    Beaulieu, P.L.5
  • 47
    • 78649616207 scopus 로고    scopus 로고
    • Dimethyl sulfoxide/potassium hydroxide: A superbase for the transition metal-free preparation of cross-coupling products
    • Yuan, Y.; Thomé, I.; Kim, S.H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Dimethyl Sulfoxide/Potassium Hydroxide: A Superbase for the Transition Metal-Free Preparation of Cross-Coupling Products. Adv. Synth. Catal. 2010, 352, 2892-2898.
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 2892-2898
    • Yuan, Y.1    Thomé, I.2    Kim, S.H.3    Chen, D.4    Beyer, A.5    Bonnamour, J.6    Zuidema, E.7    Chang, S.8    Bolm, C.9
  • 49
    • 61349149837 scopus 로고
    • Erweitertes makromolekulares kolloquium, freiburg
    • Huisgen, R.; König, H. Erweitertes Makromolekulares Kolloquium, Freiburg. Angew. Chem. 1957, 69, 268-272.
    • (1957) Angew. Chem. , vol.69 , pp. 268-272
    • Huisgen, R.1    König, H.2
  • 50
    • 0002777371 scopus 로고
    • Nucleophile aromatische substitutionen über arine
    • Huisgen, R.; Sauer, J. Nucleophile aromatische Substitutionen über Arine. Angew. Chem. 1960, 72, 91-108.
    • (1960) Angew. Chem. , vol.72 , pp. 91-108
    • Huisgen, R.1    Sauer, J.2
  • 51
    • 0343315128 scopus 로고
    • A general principle for the synthesis of heterocyclic and homocyclic compounds
    • Hrutford, B.F.; Bunnett, J.F. A General Principle for the Synthesis of Heterocyclic and Homocyclic Compounds. J. Am. Chem. Soc. 1958, 80, 2021-2022.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 2021-2022
    • Hrutford, B.F.1    Bunnett, J.F.2
  • 52
    • 0001724107 scopus 로고
    • Ring closure via aryne intermediates: A general principle of synthesis
    • Bunnett, J.F.; Hrutford, B.F. Ring Closure via Aryne Intermediates: A General Principle of Synthesis. J. Am. Chem. Soc. 1961, 83, 1691-1697.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 1691-1697
    • Bunnett, J.F.1    Hrutford, B.F.2
  • 53
    • 0001557493 scopus 로고
    • Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl) formamidines. An asymmetric route to benzopyrrocoline alkaloids
    • Sielecki, T.M.; Meyers, A.I. Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl)formamidines. An asymmetric route to benzopyrrocoline alkaloids. J. Org. Chem. 1992, 57, 3673-3676.
    • (1992) J. Org. Chem. , vol.57 , pp. 3673-3676
    • Sielecki, T.M.1    Meyers, A.I.2
  • 55
    • 64549117824 scopus 로고    scopus 로고
    • Organic synthesis "On water"
    • Chanda, A.; Fokin, V.V. Organic Synthesis "On Water". Chem. Rev. 2009, 109, 725-748.
    • (2009) Chem. Rev. , vol.109 , pp. 725-748
    • Chanda, A.1    Fokin, V.V.2
  • 56
    • 77958060431 scopus 로고    scopus 로고
    • Water: Nature's reaction enforcer - Comparative effects for organic synthesis "In-water" and "On-water"
    • Butler, R.N.; Coyne, A.G. Water: Nature's Reaction Enforcer - Comparative Effects for Organic Synthesis "In-Water" and "On-Water". Chem. Rev. 2010, 110, 6302-6337.
    • (2010) Chem. Rev. , vol.110 , pp. 6302-6337
    • Butler, R.N.1    Coyne, A.G.2
  • 57
    • 84863012202 scopus 로고    scopus 로고
    • Green chemistry oriented organic synthesis in water
    • Simon, M.-O.; Li, C.-J. Green chemistry oriented organic synthesis in water. Chem. Soc. Rev. 2012, 41, 1415-1427.
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 1415-1427
    • Simon, M.-O.1    Li, C.-J.2
  • 58
    • 79551674856 scopus 로고    scopus 로고
    • Direct transition-metal-free intramolecular C-O bond formation: Synthesis of benzoxazole derivatives
    • Peng, J.; Zong, C.; Ye, M.; Chen, T.; Gao, D.; Wang, Y.; Chen, C. Direct transition-metal-free intramolecular C-O bond formation: Synthesis of benzoxazole derivatives. Org. Biomol. Chem. 2011, 9, 1225-1230.
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 1225-1230
    • Peng, J.1    Zong, C.2    Ye, M.3    Chen, T.4    Gao, D.5    Wang, Y.6    Chen, C.7
  • 60
    • 32044438203 scopus 로고    scopus 로고
    • Acceleration of organic reactions through aqueous solvent effects
    • Pirrung, M.C. Acceleration of Organic Reactions through Aqueous Solvent Effects. Chem. Eur. J. 2006, 12, 1312-1317.
    • (2006) Chem. Eur. J. , vol.12 , pp. 1312-1317
    • Pirrung, M.C.1
  • 61
    • 34247897075 scopus 로고    scopus 로고
    • On the theory of organic catalysis "On water"
    • Jung, Y.; Marcus, R.A. On the Theory of Organic Catalysis "On Water". J. Am. Chem. Soc. 2007, 129, 5492-5502.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 5492-5502
    • Jung, Y.1    Marcus, R.A.2
  • 64
    • 71949123493 scopus 로고    scopus 로고
    • Copper-catalyzed cross-couplings with part-per-million catalyst loadings
    • Larsson, P.-F.; Correa, A.; Carril, M.; Norrby, P.-O.; Bolm, C. Copper-Catalyzed Cross-Couplings with Part-per-Million Catalyst Loadings. Angew. Chem. 2009, 121, 5801-5803;
    • (2009) Angew. Chem. , vol.121 , pp. 5801-5803
    • Larsson, P.-F.1    Correa, A.2    Carril, M.3    Norrby, P.-O.4    Bolm, C.5
  • 66
    • 84855945575 scopus 로고    scopus 로고
    • Trace metal impurities in catalysis
    • Thomé, I.; Nijs, A.; Bolm, C. Trace metal impurities in catalysis. Chem. Soc. Rev. 2012, 41, 979-987.
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 979-987
    • Thomé, I.1    Nijs, A.2    Bolm, C.3
  • 67
    • 78649507838 scopus 로고    scopus 로고
    • When is free really free?
    • Leadbeater, N.E. When is free really free? Nat. Chem. 2010, 2, 1007-1009.
    • (2010) Nat. Chem. , vol.2 , pp. 1007-1009
    • Leadbeater, N.E.1
  • 69
    • 0000634589 scopus 로고
    • Nucleophilic substitution. Linear free energy relations between reactivity and physical properties of leaving groups and substrates
    • Bartoli, G.; Todesco, P.E. Nucleophilic substitution. Linear free energy relations between reactivity and physical properties of leaving groups and substrates. Acc. Chem. Res. 1977, 10, 125-132.
    • (1977) Acc. Chem. Res. , vol.10 , pp. 125-132
    • Bartoli, G.1    Todesco, P.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.