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Volumn 133, Issue 10, 2011, Pages 3312-3315

Cooperative catalytic activation of Si-H bonds by a polar Ru-S bond: Regioselective low-temperature c-h silylation of indoles under neutral conditions by a Friedel-crafts mechanism

Author keywords

[No Author keywords available]

Indexed keywords

ADDED BASE; C-H FUNCTIONALIZATION; CATALYTIC ACTIVATION; CO-ORDINATIVELY UNSATURATED; DIHYDROGEN; ELECTROPHILES; ELECTROPHILIC AROMATIC SUBSTITUTIONS; FRIEDEL-CRAFTS; LOW TEMPERATURES; NEUTRAL CONDITIONS; REGIO-SELECTIVE; RUTHENIUM COMPLEXES; SI-H BONDS; SILYLATIONS; STERIC CONTROL; SULFUR ATOMS;

EID: 79952609033     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111483r     Document Type: Article
Times cited : (207)

References (53)
  • 1
    • 78651510629 scopus 로고    scopus 로고
    • Eds.; Springer: Heidelberg
    • For leading monographs on "C-H activation", see: Top. Curr. Chem.; Yu, J.-Q.; Shi, Z., Eds.; Springer: Heidelberg, 2010; Vol. 292.
    • (2010) Top. Curr. Chem. , vol.292
    • Yu, J.-Q.1    Shi, Z.2
  • 12
    • 54749090359 scopus 로고    scopus 로고
    • 3Si-H (with R = alkyl, aryl, and Oalkyl) in Ir(I) catalysis: Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508-7510
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7508-7510
    • Lu, B.1    Falck, J.R.2
  • 15
  • 19
    • 52149114261 scopus 로고    scopus 로고
    • For an authoritative review of transition metal-catalyzed carbon-heteroatom bond formation, see: Hartwig, J. F. Nature 2008, 455, 314-322
    • (2008) Nature , vol.455 , pp. 314-322
    • Hartwig, J.F.1
  • 22
    • 79952596551 scopus 로고    scopus 로고
    • Nagoya University: Japan,. Theoretical study: Dalton Trans. 2010
    • Sakamoto, M. PhD thesis, Nagoya University: Japan, 2010. Theoretical study: Tao, J.; Li, S. Dalton Trans. 2010, 39, 857-863
    • (2010) PhD Thesis , vol.39 , pp. 857-863
    • Sakamoto, M.1    Tao, J.2    Li, S.3
  • 26
    • 41949083723 scopus 로고    scopus 로고
    • For an excellent highlight on cooperating ligands in transition metal catalysis, see: Grützmacher, H. Angew. Chem., Int. Ed. 2008, 47, 1814-1818
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1814-1818
    • Grützmacher, H.1
  • 34
    • 79952612495 scopus 로고    scopus 로고
    • Those reactions require a base to abstract a proton from the Wheland intermediate (cf. ref 19c). Excess base also prevents the facile reverse reaction!
    • Those reactions require a base to abstract a proton from the Wheland intermediate (cf. ref 19c). Excess base also prevents the facile reverse reaction!
  • 35
    • 0342619244 scopus 로고
    • Electrophilic silylation of aromatic compounds is also referred to as "sila-Friedel-Crafts reactions", and only a handful of examples are known to date:, (intermolecular).
    • Electrophilic silylation of aromatic compounds is also referred to as "sila-Friedel-Crafts reactions", and only a handful of examples are known to date: Sollott, G. P.; Peterson, Jr., W. R. J. Am. Chem. Soc. 1967, 89, 5054 - 5056 (intermolecular).
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5054-5056
    • Sollott, G.P.1    Peterson, Jr.W.R.2
  • 39
    • 34250655628 scopus 로고    scopus 로고
    • For a review of direct transition metal-catalyzed functionalization of heterocycles, see: Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173-1193
    • (2007) Chem. Soc. Rev. , vol.36 , pp. 1173-1193
    • Seregin, I.V.1    Gevorgyan, V.2
  • 44
    • 79952607731 scopus 로고    scopus 로고
    • 2)-H bonds, are not catalytically active. We understand this as further evidence in support of our Ru-S cooperative catalysis.
    • 2)-H bonds, are not catalytically active. We understand this as further evidence in support of our Ru-S cooperative catalysis.
  • 45
    • 79952604925 scopus 로고    scopus 로고
    • Donor solvents deactivate 2, whereas non-nucleophilic solvents, i.e., hydrocarbons such as n -hexane, are tolerated.
    • Donor solvents deactivate 2, whereas non-nucleophilic solvents, i.e., hydrocarbons such as n -hexane, are tolerated.
  • 46
    • 79952594222 scopus 로고    scopus 로고
    • A color change from green (complex 2) to yellow (silane adduct 26) visualizes successful Si-H bond activation. No color change was observed with 6d or 6e.
    • A color change from green (complex 2) to yellow (silane adduct 26) visualizes successful Si-H bond activation. No color change was observed with 6d or 6e.


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