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Volumn 7, Issue 12, 2015, Pages 987-994

A manganese catalyst for highly reactive yet chemoselective intramolecular C(sp 3)-H amination

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; MANGANESE;

EID: 84947743329     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2366     Document Type: Article
Times cited : (228)

References (45)
  • 1
    • 84863494370 scopus 로고    scopus 로고
    • Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds
    • Roizen, J. L., Harvey, M. E., Du Bois, J. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds. Acc. Chem. Res. 45, 911-922 (2012).
    • (2012) Acc. Chem. Res , vol.45 , pp. 911-922
    • Roizen, J.L.1    Harvey, M.E.2    Du Bois, J.3
  • 2
    • 84857325043 scopus 로고    scopus 로고
    • Adding aliphatic C-H bond oxidations to synthesis
    • White, M. C. Adding aliphatic C-H bond oxidations to synthesis. Science 335, 807-809 (2012).
    • (2012) Science , vol.335 , pp. 807-809
    • White, M.C.1
  • 3
    • 34547732579 scopus 로고    scopus 로고
    • The road to non-heme oxoferryls and beyond
    • Que, L. Jr. The road to non-heme oxoferryls and beyond. Acc. Chem. Res. 40, 493-500 (2007).
    • (2007) Acc. Chem. Res , vol.40 , pp. 493-500
    • Que, L.1
  • 4
    • 84898843182 scopus 로고    scopus 로고
    • Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-oxo complexes
    • Nam, W., Lee, Y., Fukuzumi, S. Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-oxo complexes. Acc. Chem. Res. 47, 1146-1154 (2014).
    • (2014) Acc. Chem. Res , vol.47 , pp. 1146-1154
    • Nam, W.1    Lee, Y.2    Fukuzumi, S.3
  • 5
    • 40949096433 scopus 로고    scopus 로고
    • A predictable selective aliphatic C-H oxidation reaction for complex molecule synthesis
    • Chen, M. S., White, M. C. A predictable selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science 318, 783-787 (2007).
    • (2007) Science , vol.318 , pp. 783-787
    • Chen, M.S.1    White, M.C.2
  • 6
    • 84884871427 scopus 로고    scopus 로고
    • Catalyst-controlled aliphatic C-H oxidations with a predictive model for site-selectivity
    • Gormisky, P. E., White, M. C. Catalyst-controlled aliphatic C-H oxidations with a predictive model for site-selectivity. J. Am. Chem. Soc. 135, 14052-14055 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 14052-14055
    • Gormisky, P.E.1    White, M.C.2
  • 7
    • 84885070397 scopus 로고    scopus 로고
    • Intramolecular C(sp3)-H amination
    • Jeffrey, J. L., Sarpong, R. Intramolecular C(sp3)-H amination. Chem. Sci. 4, 4092-4106 (2013).
    • (2013) Chem. Sci , vol.4 , pp. 4092-4106
    • Jeffrey, J.L.1    Sarpong, R.2
  • 9
    • 69249129394 scopus 로고    scopus 로고
    • Catalytic C-H amination: Recent progress and future directions
    • Collet, F., Dodd, R. H., Dauban, P. Catalytic C-H amination: recent progress and future directions. Chem. Commun. 5061-5074 (2009).
    • (2009) Chem. Commun. , pp. 5061-5074
    • Collet, F.1    Dodd, R.H.2    Dauban, P.3
  • 10
    • 79959790191 scopus 로고    scopus 로고
    • Selective functionalization of saturated C-H bonds with metalloporphyrin catalysts
    • Che, C. M., Lo, V. K. Y., Zhou, C. Y., Huang, J. S. Selective functionalization of saturated C-H bonds with metalloporphyrin catalysts. Chem. Soc. Rev. 40, 1950-1975 (2011).
    • (2011) Chem. Soc. Rev , vol.40 , pp. 1950-1975
    • Che, C.M.1    Lo, V.K.Y.2    Zhou, C.Y.3    Huang, J.S.4
  • 11
    • 84856492869 scopus 로고    scopus 로고
    • Iron-catalyzed intramolecular allylic C-H amination
    • Paradine, S. M., White, M. C. Iron-catalyzed intramolecular allylic C-H amination. J. Am. Chem. Soc. 134, 2036-2039 (2012).
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 2036-2039
    • Paradine, S.M.1    White, M.C.2
  • 12
    • 84877354471 scopus 로고    scopus 로고
    • Complex N-heterocycle synthesis via ironcatalyzed, direct C-H bond amination
    • Hennessy, E. T., Betley, T. A. Complex N-heterocycle synthesis via ironcatalyzed, direct C-H bond amination. Science 340, 591-595 (2013).
    • (2013) Science , vol.340 , pp. 591-595
    • Hennessy, E.T.1    Betley, T.A.2
  • 13
    • 84897699279 scopus 로고    scopus 로고
    • Ironmediated intermolecular N-group transfer chemistry with olefinic substrates
    • Hennessy, E. T., Liu, R. Y., Iovan, D. A., Duncan, R. A., Betley, T. A. Ironmediated intermolecular N-group transfer chemistry with olefinic substrates. Chem. Sci. 5, 1526-1532 (2014).
    • (2014) Chem. Sci , vol.5 , pp. 1526-1532
    • Hennessy, E.T.1    Liu, R.Y.2    Iovan, D.A.3    Duncan, R.A.4    Betley, T.A.5
  • 14
    • 84877829179 scopus 로고    scopus 로고
    • Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations
    • Liu, Y. et al. Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations. J. Am. Chem. Soc. 135, 7194-7204 (2013).
    • (2013) J. Am. Chem. Soc , vol.135 , pp. 7194-7204
    • Liu, Y.1
  • 15
    • 80054971366 scopus 로고    scopus 로고
    • A diruthenium catalyst for selective, intramolecular allylic C-H amination: Reaction development and mechanistic insight gained through experiment and theory
    • Harvey, M. E., Musaev, D. G., Du Bois, J. A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory. J. Am. Chem. Soc. 133, 17207-17216 (2011).
    • (2011) J. Am. Chem. Soc , vol.133 , pp. 17207-17216
    • Harvey, M.E.1    Musaev, D.G.2    Du Bois, J.3
  • 16
    • 41949125347 scopus 로고    scopus 로고
    • Iron-catalyzed asymmetric olefin cis-dihydroxylation with 97% enantiomeric excess
    • Suzuki, K., Oldenburg, P. D., Que, L. Jr. Iron-catalyzed asymmetric olefin cis-dihydroxylation with 97% enantiomeric excess. Angew. Chem. Int. Ed. 47, 1887-1889 (2008).
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 1887-1889
    • Suzuki, K.1    Oldenburg, P.D.2    Que, L.3
  • 17
    • 84888809801 scopus 로고    scopus 로고
    • Cobalt precursors for high-throughput discovery of base metal asymmetric alkene hydrogenation catalysts
    • Friedfel, M. R. et al. Cobalt precursors for high-throughput discovery of base metal asymmetric alkene hydrogenation catalysts. Science 342, 1076-1080 (2013).
    • (2013) Science , vol.342 , pp. 1076-1080
    • Friedfel, M.R.1
  • 18
    • 84888789601 scopus 로고    scopus 로고
    • Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines
    • Jagadeesh, R. V. et al. Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines. Science 342, 1073-1076 (2013).
    • (2013) Science , vol.342 , pp. 1073-1076
    • Jagadeesh, R.V.1
  • 19
    • 84888782987 scopus 로고    scopus 로고
    • Amine(imine)diphosphine iron catalysts for asymmetric transfer hydrogenation of ketones and imines
    • Zuo, W., Lough, A. J., Young, F. L., Morris, R. H. Amine(imine)diphosphine iron catalysts for asymmetric transfer hydrogenation of ketones and imines. Science 342, 1080-1083 (2013).
    • (2013) Science , vol.342 , pp. 1080-1083
    • Zuo, W.1    Lough, A.J.2    Young, F.L.3    Morris, R.H.4
  • 20
    • 0001560945 scopus 로고
    • Selectivity control by axial ligand modification in manganese porphyrin catalyzed oxidations
    • Nappa, M. J., McKinney, R. J. Selectivity control by axial ligand modification in manganese porphyrin catalyzed oxidations. Inorg. Chem. 27, 3740-3745 (1988).
    • (1988) Inorg. Chem , vol.27 , pp. 3740-3745
    • Nappa, M.J.1    McKinney, R.J.2
  • 21
    • 62349133181 scopus 로고    scopus 로고
    • Oxidative cyclization of sulfamate esters using NaOCl - A metal-mediated Hoffman-Löffler-Freytag reaction
    • Zalatan, D. N., Du Bois, J. Oxidative cyclization of sulfamate esters using NaOCl-a metal-mediated Hoffman-Löffler-Freytag reaction. Synlett. 143-146 (2009).
    • (2009) Synlett , pp. 143-146
    • Zalatan, D.N.1    Du Bois, J.2
  • 22
    • 0000548724 scopus 로고
    • Hydrocarbon oxidations with oxometalloporphinates Isolation and reactions of a (porphinato)manganese(V) complex
    • Groves, J. T., Kruper, W. J., Haushalter, R. C. Hydrocarbon oxidations with oxometalloporphinates. Isolation and reactions of a (porphinato)manganese(V) complex. J. Am. Chem. Soc. 102, 6375-6377 (1980).
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6375-6377
    • Groves, J.T.1    Kruper, W.J.2    Haushalter, R.C.3
  • 23
    • 33845374759 scopus 로고
    • Shape-selective alkane hydroxylation by metalloporphyrin catalysts
    • Cook, B. R., Reinert, T. J., Suslick, K. S. Shape-selective alkane hydroxylation by metalloporphyrin catalysts. J. Am. Chem. Soc. 108, 7281-7286 (1986).
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 7281-7286
    • Cook, B.R.1    Reinert, T.J.2    Suslick, K.S.3
  • 24
    • 0000472932 scopus 로고
    • Structural characterization of a complex of manganese(V) nitrido[tetrakis(p-methoxyphenyl)porphinato]manganese(V)
    • Hill, C. J., Hollander, F. J. Structural characterization of a complex of manganese(V) nitrido[tetrakis(p-methoxyphenyl)porphinato]manganese(V). J. Am. Chem. Soc. 104, 7318-7319 (1982).
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7318-7319
    • Hill, C.J.1    Hollander, F.J.2
  • 25
    • 33645841657 scopus 로고    scopus 로고
    • Mid-to high-valent imido and nitrido complexes of iron
    • Mehn, M. P., Peters, J. C. Mid-to high-valent imido and nitrido complexes of iron. J. Inorg. Biochem. 100, 634-643 (2006).
    • (2006) J. Inorg. Biochem , vol.100 , pp. 634-643
    • Mehn, M.P.1    Peters, J.C.2
  • 26
    • 0141645556 scopus 로고    scopus 로고
    • Intramolecular aromatic amination through iron-mediated nitrene transfer
    • Jensen,M. P.,Mehn,M. P., Que, L. Jr. Intramolecular aromatic amination through iron-mediated nitrene transfer. Angew. Chem. Int. Ed. 42, 4357-4360 (2003).
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4357-4360
    • Jensen, M.P.1    Mehn, M.P.2    Que, L.3
  • 28
    • 33845550515 scopus 로고
    • Intramolecular nitrene C-H insertions mediated by transition-metal complexes as nitrogen analogues of cytochrome P-450 reactions
    • Breslow, R., Gellman, S. H. Intramolecular nitrene C-H insertions mediated by transition-metal complexes as nitrogen analogues of cytochrome P-450 reactions. J. Am. Chem. Soc. 105, 6728-6729 (1983).
    • (1983) J. Am. Chem. Soc , vol.105 , pp. 6728-6729
    • Breslow, R.1    Gellman, S.H.2
  • 29
    • 0000229761 scopus 로고
    • Redox potentials of metal phthalocyanines in non-aqueous media
    • Lever, A. B. P., Wilshire, J. P. Redox potentials of metal phthalocyanines in non-aqueous media. Can. J. Chem. 54, 2514-2516 (1976).
    • (1976) Can. J. Chem , vol.54 , pp. 2514-2516
    • Lever, A.B.P.1    Wilshire, J.P.2
  • 31
    • 62049085234 scopus 로고    scopus 로고
    • A mechanistic analysis of the Rh-catalyzed intramolecular C-H amination reaction
    • Fiori, K.W., Espino, C. G., Brodsky, B. H., Du Bois, J. A mechanistic analysis of the Rh-catalyzed intramolecular C-H amination reaction. Tetrahedron. 65, 3042-3051 (2009).
    • (2009) Tetrahedron , vol.65 , pp. 3042-3051
    • Fiori, K.W.1    Espino, C.G.2    Brodsky, B.H.3    Du Bois, J.4
  • 32
    • 53849147524 scopus 로고    scopus 로고
    • Rhodium-catalyzed amination reaction from N-tosyloxycarbamates
    • Huard, K., Lebel, H. Rhodium-catalyzed amination reaction from N-tosyloxycarbamates. Chem. Eur. J. 14, 6222-6230 (2008).
    • (2008) Chem. Eur. J , vol.14 , pp. 6222-6230
    • Huard, K.1    Lebel, H.2
  • 33
    • 69049083453 scopus 로고    scopus 로고
    • A catalytic Bronsted base strategy for intermolecular allylic C-H amination
    • Reed, S. A., Mazzotti, A. R., White, M. C. A catalytic, Bronsted base strategy for intermolecular allylic C-H amination. J. Am. Chem. Soc. 131, 11701-11706 (2009).
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 11701-11706
    • Reed, S.A.1    Mazzotti, A.R.2    White, M.C.3
  • 34
    • 38349004623 scopus 로고    scopus 로고
    • Toward a synthetically useful stereoselective C-H amination of hydrocarbons
    • Liang, C. et al. Toward a synthetically useful stereoselective C-H amination of hydrocarbons. J. Am. Chem. Soc. 130, 343-350 (2008).
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 343-350
    • Liang, C.1
  • 35
    • 84855485317 scopus 로고    scopus 로고
    • Synthesis of propargylic and allenic carbamates via the C-H amination of alkynes
    • Grigg, D. R., Rigoli, J. W., Pearce, S. D., Schomaker, J. M. Synthesis of propargylic and allenic carbamates via the C-H amination of alkynes. Org. Lett. 14, 280-283 (2012).
    • (2012) Org. Lett , vol.14 , pp. 280-283
    • Grigg, D.R.1    Rigoli, J.W.2    Pearce, S.D.3    Schomaker, J.M.4
  • 36
    • 42149120112 scopus 로고    scopus 로고
    • Catalytic metallonitrene/alkyne meta thesis: A powerful cascade process for the synthesis of nitrogen-containing molecules
    • Thornton, A. R., Blakey, S. B. Catalytic metallonitrene/alkyne metathesis: a powerful cascade process for the synthesis of nitrogen-containing molecules. J. Am. Chem. Soc. 130, 5020-5021 (2008).
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 5020-5021
    • Thornton, A.R.1    Blakey, S.B.2
  • 37
    • 34547913768 scopus 로고    scopus 로고
    • (+)-Saxitoxin: A first and second generation stereoselective synthesis
    • Fleming, J. J., McReynolds, M. D., Du Bois, J. (+)-Saxitoxin: a first and second generation stereoselective synthesis. J. Am. Chem. Soc. 129, 9964-9975 (2007).
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 9964-9975
    • Fleming, J.J.1    McReynolds, M.D.2    Du Bois, J.3
  • 38
    • 84923076544 scopus 로고    scopus 로고
    • Metal-catalysed azidation of tertiary C-H bonds suitable for late-stage functionalization
    • Sharma, A., Hartwig, J. H. Metal-catalysed azidation of tertiary C-H bonds suitable for late-stage functionalization. Nature 517, 600-604 (2015).
    • (2015) Nature , vol.517 , pp. 600-604
    • Sharma, A.1    Hartwig, J.H.2
  • 39
    • 84856714142 scopus 로고    scopus 로고
    • Intermolecular Ritter-type C-H amination of unactivated sp3 carbons
    • Michaudel, Q., Thevenet, D., Baran, P. S. Intermolecular Ritter-type C-H amination of unactivated sp3 carbons. J. Am. Chem. Soc. 134, 2547-2550 (2012).
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 2547-2550
    • Michaudel, Q.1    Thevenet, D.2    Baran, P.S.3
  • 40
    • 0037138676 scopus 로고    scopus 로고
    • C-H bond activation by cationic platinum(II) complexes: Ligand electronic and steric effects
    • Zhong, H. A., Labinger, J. A., Bercaw, J. E. C-H bond activation by cationic platinum(II) complexes: ligand electronic and steric effects. J. Am. Chem. Soc. 124, 1378-1399 (2002).
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 1378-1399
    • Zhong, H.A.1    Labinger, J.A.2    Bercaw, J.E.3
  • 41
    • 0037424821 scopus 로고    scopus 로고
    • Synthesis and reactivity of cyclic sulfamidites and sulfamidates
    • Meléndez, R. E., Lubell, W. D. Synthesis and reactivity of cyclic sulfamidites and sulfamidates. Tetrahedron 59, 2581-2616 (2003).
    • (2003) Tetrahedron , vol.59 , pp. 2581-2616
    • Meléndez, R.E.1    Lubell, W.D.2
  • 42
    • 84896496785 scopus 로고    scopus 로고
    • Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: Late-stage functionalization of an unactivated methyl group
    • Kang, T., Kim, Y., Lee, D., Wang, Z., Chang, S. Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: late-stage functionalization of an unactivated methyl group. J. Am. Chem. Soc. 136, 4141-4144 (2014).
    • (2014) J. Am. Chem. Soc , vol.136 , pp. 4141-4144
    • Kang, T.1    Kim, Y.2    Lee, D.3    Wang, Z.4    Chang, S.5
  • 43
    • 67651100837 scopus 로고    scopus 로고
    • Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells
    • Drag-Zalesinska, M. et al. Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells. Bioorg. Med. Chem. Lett. 19, 4814-4817 (2009).
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 4814-4817
    • Drag-Zalesinska, M.1
  • 44
    • 75749110908 scopus 로고    scopus 로고
    • Combined effects on selectivity in Fe-catalyzed methylene oxidation
    • Chen, M. S., White, M. C. Combined effects on selectivity in Fe-catalyzed methylene oxidation. Science 327, 566-571 (2010).
    • (2010) Science , vol.327 , pp. 566-571
    • Chen, M.S.1    White, M.C.2


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