메뉴 건너뛰기




Volumn 20, Issue 7, 2015, Pages 11676-11698

Iridium-catalysed ortho-directed deuterium labelling of aromatic esters - An experimental and theoretical study on directing group chemoselectivity

Author keywords

C H activation; Deuterium; DFT; Esters; Hydrogen isotope exchange; Iridium

Indexed keywords

DEUTERIUM; ESTER; IRIDIUM;

EID: 84938630559     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules200711676     Document Type: Article
Times cited : (26)

References (42)
  • 2
    • 78650429706 scopus 로고    scopus 로고
    • Metal-catalysed isotopic exchange labelling: 30 Years of experience in pharmaceutical R&D
    • Allen, P.H.; Hickey, M.J.; Kingston, L.P.; Wilkinson, D.J. Metal-catalysed isotopic exchange labelling: 30 years of experience in pharmaceutical R&D. J. Label. Compd. Radiopharm. 2010, 53, 731-738.
    • (2010) J. Label. Compd. Radiopharm. , vol.53 , pp. 731-738
    • Allen, P.H.1    Hickey, M.J.2    Kingston, L.P.3    Wilkinson, D.J.4
  • 3
    • 78650435552 scopus 로고    scopus 로고
    • Tritium labelling of pharmaceuticals by metal-catalysed exchange methods
    • Hesk, D.; Lavey, C.F.; McNamara, P. Tritium labelling of pharmaceuticals by metal-catalysed exchange methods. J. Label. Compd. Radiopharm. 2010, 53, 722-730.
    • (2010) J. Label. Compd. Radiopharm. , vol.53 , pp. 722-730
    • Hesk, D.1    Lavey, C.F.2    McNamara, P.3
  • 4
    • 35748972607 scopus 로고    scopus 로고
    • Organoiridium complexes for hydrogen isotope exchange labeling
    • Heys, J.R. Organoiridium complexes for hydrogen isotope exchange labeling. J. Label. Compd. Radiopharm. 2007, 50, 770-778.
    • (2007) J. Label. Compd. Radiopharm. , vol.50 , pp. 770-778
    • Heys, J.R.1
  • 5
    • 84863109632 scopus 로고    scopus 로고
    • Tritium: A coming of age for drug discovery and development ADME studies
    • Lockley, W.J.S.; McEwen, A.; Cooke, R. Tritium: A coming of age for drug discovery and development ADME studies. J. Label. Compd. Radiopharm. 2012, 55, 235-257.
    • (2012) J. Label. Compd. Radiopharm. , vol.55 , pp. 235-257
    • Lockley, W.J.S.1    McEwen, A.2    Cooke, R.3
  • 6
    • 78650487866 scopus 로고    scopus 로고
    • The development and use of novel iridium complexes as catalysts for ortho-directed hydrogen isotope exchange reactions
    • Nilsson, G.N.; Kerr, W.J. The development and use of novel iridium complexes as catalysts for ortho-directed hydrogen isotope exchange reactions. J. Label. Compd. Radiopharm. 2010, 53, 662-667.
    • (2010) J. Label. Compd. Radiopharm. , vol.53 , pp. 662-667
    • Nilsson, G.N.1    Kerr, W.J.2
  • 7
    • 84859809777 scopus 로고    scopus 로고
    • Efficient H-D Exchange Reactions Using Heterogeneous Platinum-Group Metal on Carbon-H2-D2O System
    • Sawama, Y.; Monguchi, Y.; Sajiki, H. Efficient H-D Exchange Reactions Using Heterogeneous Platinum-Group Metal on Carbon-H2-D2O System. Synlett 2012, 23, 959-972.
    • (2012) Synlett , vol.23 , pp. 959-972
    • Sawama, Y.1    Monguchi, Y.2    Sajiki, H.3
  • 9
    • 35748951582 scopus 로고    scopus 로고
    • 30 Years with ortho-directed hydrogen isotope exchange labelling
    • Lockley, W.J.S. 30 Years with ortho-directed hydrogen isotope exchange labelling. J. Label. Compd. Radiopharm. 2007, 50, 779-788.
    • (2007) J. Label. Compd. Radiopharm. , vol.50 , pp. 779-788
    • Lockley, W.J.S.1
  • 10
    • 35748980549 scopus 로고    scopus 로고
    • Synthesis of isotopically labelled compounds at Schering-Plough, an historical perspective
    • Hesk, D.; McNamara, P. Synthesis of isotopically labelled compounds at Schering-Plough, an historical perspective. J. Label. Compd. Radiopharm. 2007, 50, 875-887.
    • (2007) J. Label. Compd. Radiopharm. , vol.50 , pp. 875-887
    • Hesk, D.1    McNamara, P.2
  • 11
    • 0034118057 scopus 로고    scopus 로고
    • Chemical derivatization and the selection of deuterated internal standard for quantitative determination - Methamphetamine example
    • Lin, D.; Chang, W. Chemical derivatization and the selection of deuterated internal standard for quantitative determination - Methamphetamine example. J. Anal. Toxicol. 2000, 24, 275-280.
    • (2000) J. Anal. Toxicol. , vol.24 , pp. 275-280
    • Lin, D.1    Chang, W.2
  • 12
    • 78650487017 scopus 로고    scopus 로고
    • Pd- and Pt-catalyzed H/D exchange methods and their application for internal MS standard preparation from a Sanofi-Aventis perspective
    • Atzrodt, J.; Derdau, V. Pd- and Pt-catalyzed H/D exchange methods and their application for internal MS standard preparation from a Sanofi-Aventis perspective. J. Label. Compd. Radiopharm. 2010, 53, 674-685.
    • (2010) J. Label. Compd. Radiopharm. , vol.53 , pp. 674-685
    • Atzrodt, J.1    Derdau, V.2
  • 13
    • 38349036019 scopus 로고    scopus 로고
    • Applications of deuterium isotope effects for probing aspects of reactions involving oxidative addition and reductive elimination of H-H and C-H bonds
    • Parkin, G. Applications of deuterium isotope effects for probing aspects of reactions involving oxidative addition and reductive elimination of H-H and C-H bonds. J. Label. Compd. Radiopharm. 2007, 50, 1088-1114.
    • (2007) J. Label. Compd. Radiopharm. , vol.50 , pp. 1088-1114
    • Parkin, G.1
  • 14
    • 38349078615 scopus 로고    scopus 로고
    • Transition metal dihydrogen complexes: Isotope effects on reactivity and structure
    • Heinekey, D.M. Transition metal dihydrogen complexes: Isotope effects on reactivity and structure. J. Label. Compd. Radiopharm. 2007, 50, 1063-1071.
    • (2007) J. Label. Compd. Radiopharm. , vol.50 , pp. 1063-1071
    • Heinekey, D.M.1
  • 15
    • 84856292998 scopus 로고    scopus 로고
    • Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile
    • Quasdorf, K.W.; Huters, A.D.; Lodewyk, M.W.; Tantillo, D.J.; Garg, N.K. Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile. J. Am. Chem. Soc. 2012, 134, 1396-1399.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 1396-1399
    • Quasdorf, K.W.1    Huters, A.D.2    Lodewyk, M.W.3    Tantillo, D.J.4    Garg, N.K.5
  • 18
    • 84907550552 scopus 로고    scopus 로고
    • Anion effects to deliver enhanced iridium catalysts for hydrogen isotope exchange processes
    • Kennedy, A.R.; Kerr, W.J.; Moir, R.; Reid, M. Anion effects to deliver enhanced iridium catalysts for hydrogen isotope exchange processes. Org. Biomol. Chem. 2014, 12, 7927-7931.
    • (2014) Org. Biomol. Chem. , vol.12 , pp. 7927-7931
    • Kennedy, A.R.1    Kerr, W.J.2    Moir, R.3    Reid, M.4
  • 19
    • 84923934527 scopus 로고    scopus 로고
    • Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles
    • Atzrodt, J.; Derdau, V.; Kerr, W.J.; Reid, M.; Rojahn, P.; Weck, R. Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles. Tetrahedron 2015, 71, 1924-1929.
    • (2015) Tetrahedron , vol.71 , pp. 1924-1929
    • Atzrodt, J.1    Derdau, V.2    Kerr, W.J.3    Reid, M.4    Rojahn, P.5    Weck, R.6
  • 20
    • 84923910059 scopus 로고    scopus 로고
    • Iridium-Catalyzed C-H Activation and Deuteration of Primary Sulfonamides: An Experimental and Computational Study
    • Kerr, W.J.; Reid, M.; Tuttle, T. Iridium-Catalyzed C-H Activation and Deuteration of Primary Sulfonamides: An Experimental and Computational Study. ACS Catal. 2015, 5, 402-410.
    • (2015) ACS Catal. , vol.5 , pp. 402-410
    • Kerr, W.J.1    Reid, M.2    Tuttle, T.3
  • 21
    • 84894373990 scopus 로고    scopus 로고
    • Application of Neutral Iridium(I) N-Heterocyclic Carbene Complexes in ortho-Directed Hydrogen Isotope Exchange
    • Cochrane, A.R.; Irvine, S.; Kerr, W.J.; Reid, M.; Andersson, S.; Nilsson, G.N. Application of Neutral Iridium(I) N-Heterocyclic Carbene Complexes in ortho-Directed Hydrogen Isotope Exchange. J. Label. Compd. Radiopharm. 2013, 56, 451-454.
    • (2013) J. Label. Compd. Radiopharm. , vol.56 , pp. 451-454
    • Cochrane, A.R.1    Irvine, S.2    Kerr, W.J.3    Reid, M.4    Andersson, S.5    Nilsson, G.N.6
  • 22
    • 84919343697 scopus 로고    scopus 로고
    • Iridium(I)-Catalyzed Regioselective C-H Activation and Hydrogen-Isotope Exchange of Non-aromatic Unsaturated Functionality
    • Kerr, W.J.; Mudd, R.J.; Paterson, L.C.; Brown, J.A. Iridium(I)-Catalyzed Regioselective C-H Activation and Hydrogen-Isotope Exchange of Non-aromatic Unsaturated Functionality. Chem. Eur. J. 2014, 20, 14604-14607.
    • (2014) Chem. Eur. J. , vol.20 , pp. 14604-14607
    • Kerr, W.J.1    Mudd, R.J.2    Paterson, L.C.3    Brown, J.A.4
  • 24
    • 0035851237 scopus 로고    scopus 로고
    • The scope and limitations of deuteration mediated by Crabtree's catalyst
    • Ellames, G.; Gibson, J.; Herbert, J.; McNeill, A. The scope and limitations of deuteration mediated by Crabtree's catalyst. Tetrahedron 2001, 57, 9487-9497.
    • (2001) Tetrahedron , vol.57 , pp. 9487-9497
    • Ellames, G.1    Gibson, J.2    Herbert, J.3    McNeill, A.4
  • 25
    • 0027466617 scopus 로고
    • Deuterium exchange labelling of substituted aromatics using IrH2(Me2CO)2(PPh3)2BF4
    • Heys, J.R.; Shu, A.Y.L.; Senderoff, S.G.; Phillips, N.M. Deuterium exchange labelling of substituted aromatics using [IrH2(Me2CO)2(PPh3)2BF4. J. Label. Compd. Radiopharm. 1993, 33, 431-438.
    • (1993) J. Label. Compd. Radiopharm. , vol.33 , pp. 431-438
    • Heys, J.R.1    Shu, A.Y.L.2    Senderoff, S.G.3    Phillips, N.M.4
  • 26
    • 0030295952 scopus 로고    scopus 로고
    • Organoiridium catalyzed hydrogen isotope exchange: Ligand effects on catalyst activity and regioselectivity
    • Shu, A.; Chen, W.; Heys, J. Organoiridium catalyzed hydrogen isotope exchange: ligand effects on catalyst activity and regioselectivity. J. Organomet. Chem. 1996, 524, 87-93.
    • (1996) J. Organomet. Chem. , vol.524 , pp. 87-93
    • Shu, A.1    Chen, W.2    Heys, J.3
  • 27
    • 84908061261 scopus 로고    scopus 로고
    • Regioselective ruthenium catalysed H-D exchange using D2O as the deuterium source
    • Piola, L.; Fernández-Salas, J.A.; Manzini, S.; Nolan, S.P. Regioselective ruthenium catalysed H-D exchange using D2O as the deuterium source. Org. Biomol. Chem. 2014, 12, 8683-8688.
    • (2014) Org. Biomol. Chem. , vol.12 , pp. 8683-8688
    • Piola, L.1    Fernández-Salas, J.A.2    Manzini, S.3    Nolan, S.P.4
  • 28
    • 0028956348 scopus 로고
    • Deuteration of Acetanilides and Other Substituted Aromatics Using [Ir(COD)(Cy3P)PyPF6 as Catalyst
    • Hesk, D.; Das, P.R.; Evans, B. Deuteration of Acetanilides and Other Substituted Aromatics Using [Ir(COD)(Cy3P)Py)PF6 as Catalyst. J. Label. Compd. Radiopharm. 1995, 36, 497-502.
    • (1995) J. Label. Compd. Radiopharm. , vol.36 , pp. 497-502
    • Hesk, D.1    Das, P.R.2    Evans, B.3
  • 30
    • 4243664295 scopus 로고
    • A survey of Hammett substituent constants and resonance and field parameters
    • Hansch, C.; Leo, A.; Taft, R.W. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195.
    • (1991) Chem. Rev. , vol.91 , pp. 165-195
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 31
    • 1542554559 scopus 로고
    • Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kinetics
    • Seeman, J.I. Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kinetics. Chem. Rev. 1983, 83, 83-134.
    • (1983) Chem. Rev. , vol.83 , pp. 83-134
    • Seeman, J.I.1
  • 32
    • 69949117215 scopus 로고    scopus 로고
    • Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and Chlorides
    • Shang, R.; Fu, Y.; Li, J.B.; Zhang, S.L.; Guo, Q.X.; Liu, L. Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and Chlorides. J. Am. Chem. Soc. 2009, 131, 5738-5379.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5738-15379
    • Shang, R.1    Fu, Y.2    Li, J.B.3    Zhang, S.L.4    Guo, Q.X.5    Liu, L.6
  • 33
    • 84938613108 scopus 로고
    • Cosmetic Preparations with Alkoxybenzoic Acid Esters as Inflammation Inhibitors and Method
    • U.S. Patent filed 22 April 1977, and issued 23 January
    • Moller, H.; Thimm, H.J. Cosmetic Preparations with Alkoxybenzoic Acid Esters as Inflammation Inhibitors and Method. U.S. Patent 4,136,165, filed 22 April 1977, and issued 23 January 1979.
    • (1979)
    • Moller, H.1    Thimm, H.J.2
  • 34
    • 19744380541 scopus 로고    scopus 로고
    • Facile oxidative conversion of alcohols to esters usingmolecular iodine
    • Mori, N.; Togo, H. Facile oxidative conversion of alcohols to esters usingmolecular iodine. Tetrahedron 2005, 61, 5915-5925.
    • (2005) Tetrahedron , vol.61 , pp. 5915-5925
    • Mori, N.1    Togo, H.2
  • 35
    • 0035974358 scopus 로고    scopus 로고
    • A mild and selective method for the cleavage of tert-butyl esters
    • Jackson, R.W. A mild and selective method for the cleavage of tert-butyl esters. Tetrahedron Lett. 2001, 42, 5163-5165.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5163-5165
    • Jackson, R.W.1
  • 36
    • 33947434926 scopus 로고
    • Ionization of Organic Esters in Sulfuric Acid. II. Alkyl Oxygen Fission
    • Kuh, L.P. Ionization of Organic Esters in Sulfuric Acid. II. Alkyl Oxygen Fission. J. Am. Chem. Soc. 1949, 71, 1575-1577.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 1575-1577
    • Kuh, L.P.1
  • 39
    • 0042113153 scopus 로고
    • Self-consistent equations including exchange and correlation effects
    • Kohn, W.; Sham, L. Self-consistent equations including exchange and correlation effects. Phys. Rev. 1965, 140, 1133-1138.
    • (1965) Phys. Rev. , vol.140 , pp. 1133-1138
    • Kohn, W.1    Sham, L.2
  • 40
    • 43049141516 scopus 로고    scopus 로고
    • The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other function
    • Zhao, Y.; Truhlar, D.G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function. Theor. Chem. Acc. 2008, 120, 215-241.
    • (2008) Theor. Chem. Acc. , vol.120 , pp. 215-241
    • Zhao, Y.1    Truhlar, D.G.2
  • 41
    • 11744322674 scopus 로고
    • Energy-adjusted ab initio pseudopotentials for the second and third row transition elements
    • Andrae, D.; Häußerman, U.; Dolg, M.; Stoll, H.; Preuß, H. Energy-adjusted ab initio pseudopotentials for the second and third row transition elements. Theor. Chim. Acta 1990, 77, 123-141.
    • (1990) Theor. Chim. Acta , vol.77 , pp. 123-141
    • Andrae, D.1    Häußerman, U.2    Dolg, M.3    Stoll, H.4    Preuß, H.5
  • 42
    • 84961980477 scopus 로고    scopus 로고
    • Quantum Mechanical Continuum Solvation Models
    • Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models. Chem. Rev. 2005, 105, 2999-3093.
    • (2005) Chem. Rev. , vol.105 , pp. 2999-3093
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.