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Volumn 13, Issue 32, 2007, Pages 9115-9126

Up to seven-component adducts by unprecedented multiple alkyne and carbonyl insertions in the metal-carbon bond of chromium alkoxy alkynyl carbene complexes

Author keywords

Alkyne insertion carbenes; Carbonyl compounds; Cyclopentenones; Multicomponent reactions

Indexed keywords

CHEMICAL BONDS; CHROMIUM COMPOUNDS; LIGANDS; METAL COMPLEXES; REACTION KINETICS;

EID: 36049041934     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700776     Document Type: Article
Times cited : (11)

References (62)
  • 1
    • 84890597202 scopus 로고    scopus 로고
    • Eds, J. Zhu, H. Bienaymé, Wiley-VCH
    • a) Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, 2005;
    • (2005) Multicomponent Reactions
  • 3
    • 17144366282 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1602-1634;
    • (2005) Chem. Int. Ed , vol.44 , pp. 1602-1634
    • Angew1
  • 9
    • 2542509173 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
    • (2000) Chem. Int. Ed , vol.39 , pp. 3168-3210
    • Angew1
  • 14
  • 15
    • 33745712296 scopus 로고    scopus 로고
    • Selected recent reviews: a J. W. Herndon, Coord. Chem. Rev. 2006, 250, 1889-1964;
    • Selected recent reviews: a) J. W. Herndon, Coord. Chem. Rev. 2006, 250, 1889-1964;
  • 19
    • 36049033792 scopus 로고    scopus 로고
    • 3964-4002; books
    • Angew. Chem. Int. Ed. 2000, 39, 3964-4002; books:
    • (2000) Angew. Chem. Int. Ed , vol.39
  • 20
    • 36048964625 scopus 로고    scopus 로고
    • Metal Carbenes in Organic Synthesis (Ed. : K. H. Dötz) in Topics in Organometallic Chemistry, 13, Wiley, 2004;
    • a) Metal Carbenes in Organic Synthesis (Ed. : K. H. Dötz) in Topics in Organometallic Chemistry, Vol. 13, Wiley, 2004;
  • 23
    • 33847086170 scopus 로고    scopus 로고
    • The ability of several tungsten carbene complexes to initiate alkyne polymerization has been known for long time, T. J. Katz, S. J. Lee, J. Am. Chem. Soc. 1980, 102, 422-424
    • The ability of several tungsten carbene complexes to initiate alkyne polymerization has been known for long time : T. J. Katz, S. J. Lee, J. Am. Chem. Soc. 1980, 102, 422-424.
  • 30
    • 36049007236 scopus 로고    scopus 로고
    • The incorporation of three units of a terminal aromatic alkyne to a 3-dimethylamino-3-trimethylsilylpropylidenchromium(0) complex has been reported: a) F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669-1671;
    • The incorporation of three units of a terminal aromatic alkyne to a 3-dimethylamino-3-trimethylsilylpropylidenchromium(0) complex has been reported: a) F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669-1671;
  • 32
    • 84989599453 scopus 로고
    • up to five units of alkyne inserted in a two heteroatom stabilized anionic chromium(0) carbene complex
    • b) F. Stein, M. Duetsch, M. Noltemeyer, A. de Meijere. Synlett 1993, 486-488; up to five units of alkyne inserted in a two heteroatom stabilized anionic chromium(0) carbene complex:
    • (1993) Synlett , pp. 486-488
    • Stein, F.1    Duetsch, M.2    Noltemeyer, M.3    de Meijere, A.4
  • 33
    • 0031206037 scopus 로고    scopus 로고
    • C. Álvarez-Toledano, O. Baldovino, G. Espinoza, R. A. Toscano, R. Gutiérrez-Pérez, O. García-Mellado, J. Organomet. Chem. 1997, 540, 41-49. For the nickel(0)-mediated incorporation of up to three terminal alkyne units into chromium carbene complexes:
    • c) C. Álvarez-Toledano, O. Baldovino, G. Espinoza, R. A. Toscano, R. Gutiérrez-Pérez, O. García-Mellado, J. Organomet. Chem. 1997, 540, 41-49. For the nickel(0)-mediated incorporation of up to three terminal alkyne units into chromium carbene complexes:
  • 35
    • 0041305921 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3008-3011.
    • (2003) Chem. Int. Ed , vol.42 , pp. 3008-3011
    • Angew1
  • 36
    • 36049009464 scopus 로고    scopus 로고
    • Compound 4a: C32H38CrO5; M τ, 554.6; crystal size, 0.50 × 0.45 × 0.27 mm 3; monoclinic; P21/n; a, 9.0928(4, b, 18.2604(8, c, 16.9883(8) Å α, 90.000(1, β, 95.635(1, γ, 90.000(1)°; V, 2807.08(4) Å3; Z, 4; ρ= 1.312 Mgm-3; μ, 0.447 mm-1; λ, 0.71073 Å; T= 100(2) K; 2θ;mat, 56.6; reflections collected/unique 17757/6623; R(int, 0.025, final R indices [I > 2σ(I, R1, 0.039, wR 2, 0.095, R indices (all data) R1, 0.066, wR2, 0.108, Compound 9, isomer B: C47H38CrO4; Mr, 718.81; crystal size, 0.22 × 0.15 × 0.07 mm 3; triclinic; P1̄, a, 11.4230(17, b, 12.681(2, c, 13.9518(15) Å; α, 78.434(12, β, 79.714(11, γ, 72.161(14)°; V= 1869.8(5) Å
    • 2 = 0.116; CCDC-616298 (4a), -616299 (4f isomer B) and -648 137 (9 isomer B) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.cccdc.cam.ac.uk/data_request/cif.
  • 39
    • 0031009190 scopus 로고    scopus 로고
    • Pentacarbonyl alkyne-carbene complexes and more rigid tetracarbonyl alkyne-chelated ones have also been isolated and proposed as intermediates in a bimetal-assisted intermolecular insertion, leading finally to dimerization and forming centrosymmetric chrysenes: F. Hohmann, S. Siemoneit, M. Nieger, S. Kotila, K. H. Dötz, Chem. Eur. J. 1997, 3, 853-859
    • Pentacarbonyl alkyne-carbene complexes and more rigid tetracarbonyl alkyne-chelated ones have also been isolated and proposed as intermediates in a bimetal-assisted intermolecular insertion, leading finally to dimerization and forming centrosymmetric chrysenes: F. Hohmann, S. Siemoneit, M. Nieger, S. Kotila, K. H. Dötz, Chem. Eur. J. 1997, 3, 853-859.
  • 40
    • 33745119967 scopus 로고    scopus 로고
    • S. Ma. Z. Gu, Angew. Chem. 2005, 117, 7680-7685;
    • (2005) Angew. Chem , vol.117 , pp. 7680-7685
    • Gu, S.M.Z.1
  • 41
    • 28244482315 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 7512-7517.
    • (2005) Chem. Int. Ed , vol.44 , pp. 7512-7517
    • Angew1
  • 42
    • 36048950323 scopus 로고    scopus 로고
    • For a recent 1,2-metal migration in FCC chemistry see: a T. Asakura, T. Kojima, T. Miura, N. Iwasawa, Angew. Chem. 2006, 118, 7028-7031;
    • For a recent 1,2-metal migration in FCC chemistry see: a) T. Asakura, T. Kojima, T. Miura, N. Iwasawa, Angew. Chem. 2006, 118, 7028-7031;
  • 43
    • 33750490755 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6874-6877;
    • (2006) Chem. Int. Ed , vol.45 , pp. 6874-6877
    • Angew1
  • 44
    • 0000717018 scopus 로고    scopus 로고
    • for examples of 1,2- and 1,3-chromium migrations in FCC chemistry, respectively, see: b J. Barluenga, M. Tomás, E. Rubio, J. A. López-Pelegrín, S. García-Granda, P. Pertierra, J. Am. Chem. Soc. 1996, 118, 695-696;
    • for examples of 1,2- and 1,3-chromium migrations in FCC chemistry, respectively, see: b) J. Barluenga, M. Tomás, E. Rubio, J. A. López-Pelegrín, S. García-Granda, P. Pertierra, J. Am. Chem. Soc. 1996, 118, 695-696;
  • 46
    • 36048989429 scopus 로고    scopus 로고
    • For an example of the more common exo-regioselective intramolecular insertion of an alkyne in an anionic oxycarbene complex see: H. Rudler, A. Parlier, V. Certal, J. Vaissermann, Angew. Chem. 2000, 112, 3559-3561;
    • For an example of the more common exo-regioselective intramolecular insertion of an alkyne in an anionic oxycarbene complex see: H. Rudler, A. Parlier, V. Certal, J. Vaissermann, Angew. Chem. 2000, 112, 3559-3561;
  • 48
    • 0000970845 scopus 로고    scopus 로고
    • The insertions of carbonyl ligands in carbonyl metallate complexes have been previously described for different metals: Ni: a E. J. Corey, L. S. Hegedus, J. Am. Chem. Soc. 1969, 91, 4926-4928; Fe
    • The insertions of carbonyl ligands in carbonyl metallate complexes have been previously described for different metals: Ni: a) E. J. Corey, L. S. Hegedus, J. Am. Chem. Soc. 1969, 91, 4926-4928; Fe:
  • 54
    • 0346789525 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5860-5863.
    • (2003) Chem. Int. Ed , vol.42 , pp. 5860-5863
    • Angew1
  • 55
    • 0000643207 scopus 로고    scopus 로고
    • As suggested by one of the reviewers, the transformation of XI into XIV could also proceed via a vinylidene complex and subsequent alkenyl-vinylidene coupling. This also could explain the different product types in the reaction of 3 a with internal and terminal alkynes. However, we are not aware of such behaviour for chromium, although it is well documented for other metals, such as osmium: D. Huang, M. Oliván, J. C. Huffman, O. Eisenstein, K. G. Caulton Organometallics 1998, 17, 4700-4706.
    • As suggested by one of the reviewers, the transformation of XI into XIV could also proceed via a vinylidene complex and subsequent alkenyl-vinylidene coupling. This also could explain the different product types in the reaction of 3 a with internal and terminal alkynes. However, we are not aware of such behaviour for chromium, although it is well documented for other metals, such as osmium: D. Huang, M. Oliván, J. C. Huffman, O. Eisenstein, K. G. Caulton Organometallics 1998, 17, 4700-4706.
  • 59
    • 36049027529 scopus 로고    scopus 로고
    • Ph.D. Thesis, Universidad de Oviedo
    • M. A. Palomero, Ph.D. Thesis, Universidad de Oviedo 2002, p. 217.
    • (2002) , pp. 217
    • Palomero, M.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.