메뉴 건너뛰기




Volumn , Issue , 2008, Pages 713-741

Hydrogen-Mediated Carbon-Carbon Bond Formation Catalyzed by Rhodium

Author keywords

Aldolization; Electrophilicity; Imines; Rhodium; Structural homology

Indexed keywords


EID: 84890984309     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619382.ch22     Document Type: Chapter
Times cited : (8)

References (148)
  • 1
    • 0000944975 scopus 로고
    • For use of alkenes as nucleophilic partners in catalytic reductive couplings, see:
    • For use of alkenes as nucleophilic partners in catalytic reductive couplings, see: N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 1995, 117, 6785;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6785
    • Kablaoui, N.M.1    Buchwald, S.L.2
  • 4
    • 0030861563 scopus 로고    scopus 로고
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to aldehydes, see:
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to aldehydes, see: E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9065
    • Oblinger, E.1    Montgomery, J.2
  • 14
    • 0037471214 scopus 로고    scopus 로고
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to imines, see
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to imines, see: S.J. Patel, T.F. Jamison, Angew. Chem. Int. Ed. 2003, 42, 1364.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1364
    • Patel, S.J.1    Jamison, T.F.2
  • 15
    • 0033537060 scopus 로고    scopus 로고
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to imines, see:
    • For use of alkynes as nucleophilic partners in catalytic hydrometallative reductive couplings to imines, see: M.V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11139
    • Chevliakov, M.V.1    Montgomery, J.2
  • 18
    • 0000191874 scopus 로고
    • For use of conjugated enones as nucleo-philic partners in catalytic intermolecular reductive couplings to aldehydes, see:
    • For use of conjugated enones as nucleo-philic partners in catalytic intermolecular reductive couplings to aldehydes, see: A. Revis, T. K. Hilty, Tetrahedron Lett. 1987, 28, 4809;
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4809
    • Revis, A.1    Hilty, T.K.2
  • 27
    • 0034803441 scopus 로고    scopus 로고
    • For use of conjugated enones as nucleo-philic partners in catalytic intramolecular reductive couplings to aldehydes, see:
    • For use of conjugated enones as nucleo-philic partners in catalytic intramolecular reductive couplings to aldehydes, see: T.-G. Baik, A.L. Luis, L.-C. Wang, M.J. Krische, J. Am. Chem. Soc. 2001, 123, 5112;
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5112
    • Baik, T.-G.1    Luis, A.L.2    Wang, L.-C.3    Krische, M.J.4
  • 32
    • 0041382872 scopus 로고    scopus 로고
    • For use of conjugated enones as nucleo-philic partners in catalytic intermolecular reductive couplings to aldimines, see:
    • For use of conjugated enones as nucleo-philic partners in catalytic intermolecular reductive couplings to aldimines, see: J.A. Townes, M.A. Evans, J. Queffe-lec, S. J. Taylor, J. P. Morken, Org. Lett. 2002, 4, 2537;
    • (2002) Org. Lett. , vol.4 , pp. 2537
    • Townes, J.A.1    Evans, M.A.2    Queffe-lec, J.3    Taylor, S.J.4    Morken, J.P.5
  • 34
    • 0010456977 scopus 로고
    • For use of conjugated dienes as nucleo-philic partners in catalytic intramolecular reductive couplings to aldehydes, see:
    • For use of conjugated dienes as nucleo-philic partners in catalytic intramolecular reductive couplings to aldehydes, see: Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Tagaki, M. Mori, J. Am. Chem. Soc. 1994, 116, 9771;
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9771
    • Sato, Y.1    Takimoto, M.2    Hayashi, K.3    Katsuhara, T.4    Tagaki, K.5    Mori, M.6
  • 41
    • 0032577043 scopus 로고    scopus 로고
    • For use of conjugated dienes as nucleo-philic partners in catalytic intermolecular reductive couplings to aldehydes, see:
    • For use of conjugated dienes as nucleo-philic partners in catalytic intermolecular reductive couplings to aldehydes, see: M. Kimura, A. Ezoe, K. Shibata, Y. Tamaru, J. Am. Chem. Soc. 1998, 120, 4033;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4033
    • Kimura, M.1    Ezoe, A.2    Shibata, K.3    Tamaru, Y.4
  • 48
    • 7744226165 scopus 로고    scopus 로고
    • For use of conjugated dienes as nucleo-philic partners in catalytic intermolecular reductive couplings to aldimines, see:
    • For use of conjugated dienes as nucleo-philic partners in catalytic intermolecular reductive couplings to aldimines, see: M. Kimura, A. Miyachi, K. Kojima, S. Tanaka, Y. Tamaru, J. Am. Chem. Soc. 2004, 126, 14360.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 14360
    • Kimura, M.1    Miyachi, A.2    Kojima, K.3    Tanaka, S.4    Tamaru, Y.5
  • 49
    • 1842607439 scopus 로고    scopus 로고
    • For use of conjugated enynes as nucleophilic partners in catalytic intermolecular reductive couplings to aldehydes, see:
    • For use of conjugated enynes as nucleophilic partners in catalytic intermolecular reductive couplings to aldehydes, see: K. M. Miller, T. Luanphaisarnnont, C. Molinaro, T. F. Jamison, J. Am. Chem. Soc. 2004, 126, 4130.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4130
    • Miller, K.M.1    Luanphaisarnnont, T.2    Molinaro, C.3    Jamison, T.F.4
  • 50
    • 0026418434 scopus 로고
    • For reviews on atom economy, see:
    • For reviews on atom economy, see: B.M. Trost, Science 1991, 254, 1471;
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 57
    • 0037393960 scopus 로고    scopus 로고
    • For recent reviews on alkene hydrofor-mylation and the Fischer-Tropsch reaction, see:
    • For recent reviews on alkene hydrofor-mylation and the Fischer-Tropsch reaction, see: B. Breit, Acc. Chem. Res. 2003, 36, 264;
    • (2003) Acc. Chem. Res. , vol.36 , pp. 264
    • Breit, B.1
  • 61
    • 0000193074 scopus 로고
    • Prior to our work, two examples of hydrogen-mediated C-C bond formation under CO-free conditions are reported:
    • Prior to our work, two examples of hydrogen-mediated C-C bond formation under CO-free conditions are reported: G.A. Molander, J.O. Hoberg J. Am. Chem. Soc. 1992, 114, 3123;
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3123
    • Molander, G.A.1    Hoberg, J.O.2
  • 63
    • 0002045580 scopus 로고
    • For reviews on the heterolytic activation of elemental hydrogen, see:
    • For reviews on the heterolytic activation of elemental hydrogen, see: P. J. Brothers, Prog. Inorg. Chem. 1981, 28, 1;
    • (1981) Prog. Inorg. Chem. , vol.28 , pp. 1
    • Brothers, P.J.1
  • 65
    • 0034641228 scopus 로고    scopus 로고
    • Rh(III)-metallocycles derived from 1, 6-enynes are postulated as reactive intermediates in catalytic [4+2] and [5+2] cycloadditions, Pauson-Khand reactions and cycloisomerizations:, and references cited therein
    • Rh(III)-metallocycles derived from 1, 6-enynes are postulated as reactive intermediates in catalytic [4+2] and [5+2] cycloadditions, Pauson-Khand reactions and cycloisomerizations: P. Cao, B. Wang, X. Zhang, J. Am. Chem. Soc. 2000, 122, 64901 and references cited therein.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 64901
    • Cao, P.1    Wang, B.2    Zhang, X.3
  • 68
    • 0012183059 scopus 로고
    • For a review, see:
    • For a review, see: L. Marko, Pure Appl. Chem. 1979, 51, 2211.
    • (1979) Pure Appl. Chem. , vol.51 , pp. 2211
    • Marko, L.1
  • 69
    • 33847797644 scopus 로고
    • Monohydride formation by deprotonation of a dihydride intermediate is known for cationic Rh-complexes:
    • Monohydride formation by deprotonation of a dihydride intermediate is known for cationic Rh-complexes: R.R. Schrock, J.A. Osborn, J. Am. Chem. Soc. 1976, 98, 2134;
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2134
    • Schrock, R.R.1    Osborn, J.A.2
  • 72
    • 0002124260 scopus 로고
    • Transition Metal Hydrides
    • For a review of the acidity of metal hydrides, see: in: A. Dedieu (Ed.), New York
    • For a review of the acidity of metal hydrides, see: J.R. Norton, in: A. Dedieu (Ed.), Transition Metal Hydrides. New York, 1992, pp. 309.
    • (1992) , pp. 309
    • Norton, J.R.1
  • 73
    • 37049124551 scopus 로고
    • 2 has been suggested, but likely involves an intermediate dihy-dride:
    • 2 has been suggested, but likely involves an intermediate dihy-dride: D. Evans, J.A. Osborn, G. Wilkinson, J. Chem. Soc. A 1968, 3133.
    • (1968) J. Chem. Soc. A , pp. 3133
    • Evans, D.1    Osborn, J.A.2    Wilkinson, G.3
  • 74
    • 5444235959 scopus 로고    scopus 로고
    • For earlier reviews encompassing aspects ofthis work, see:
    • For earlier reviews encompassing aspects ofthis work, see: H.-Y. Jang, M.J. Krische, Eur. J. Org. Chem. 2004, 3953;
    • (2004) Eur. J. Org. Chem. , pp. 3953
    • Jang, H.-Y.1    Krische, M.J.2
  • 88
    • 84941207091 scopus 로고
    • For excellent reviews, see
    • For excellent reviews, see: J. Halpern, Asymm. Synth. 1985, 5, 41;
    • (1985) Asymm. Synth. , vol.5 , pp. 41
    • Halpern, J.1
  • 91
    • 0033552258 scopus 로고    scopus 로고
    • A method for the stoichiometric addition of metallo-aldehyde enolates to ketones has recently been reported:
    • A method for the stoichiometric addition of metallo-aldehyde enolates to ketones has recently been reported: K. Yachi, H. Shinokubo, K. Oshima, J. Am. Chem. Soc. 1999, 121, 9465.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9465
    • Yachi, K.1    Shinokubo, H.2    Oshima, K.3
  • 93
    • 0000456862 scopus 로고
    • The failure of tris(dialkylamino)sulfo-nium enolates to react with aldehydes is attributed to unfavorable enolate-aldolate equilibria
    • The failure of tris(dialkylamino)sulfo-nium enolates to react with aldehydes is attributed to unfavorable enolate-aldolate equilibria: R. Noyori, J. Sakata, M. Nishizawa, J. Am. Chem. Soc. 1980, 102, 1223;
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 1223
    • Noyori, R.1    Sakata, J.2    Nishizawa, M.3
  • 101
    • 0038682049 scopus 로고    scopus 로고
    • For a recent discussion, see: and references therein
    • For a recent discussion, see: T. C. Morrill, C.A. D'Souza, Organometallics 2003, 22, 1626 and references therein.
    • (2003) Organometallics , vol.22 , pp. 1626
    • Morrill, T.C.1    D'Souza, C.A.2
  • 108
    • 33845279184 scopus 로고
    • For metal-catalyzed cyclization of 1, 6-and 1, 7-diynes, see:
    • For metal-catalyzed cyclization of 1, 6-and 1, 7-diynes, see: B.M. Trost, D.C. Lee, J. Am. Chem. Soc. 1988, 110, 7255;
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7255
    • Trost, B.M.1    Lee, D.C.2
  • 123
    • 0002524474 scopus 로고
    • For reviews encompassing the Pd-cata-lyzed cycloisomerization and reductive cyclization of 1, 6-enynes, see:
    • For reviews encompassing the Pd-cata-lyzed cycloisomerization and reductive cyclization of 1, 6-enynes, see: B. M. Trost, Acc. Chem. Res. 1990, 23, 34;
    • (1990) Acc. Chem. Res. , vol.23 , pp. 34
    • Trost, B.M.1
  • 127
    • 0033541036 scopus 로고    scopus 로고
    • For selected examples of the cycloisomer-ization of 1, 6-enynes catalyzed by metals other than palladium, see: Titanium:
    • For selected examples of the cycloisomer-ization of 1, 6-enynes catalyzed by metals other than palladium, see: Titanium: S.J. Sturla, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc. 1999, 121, 1976;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1976
    • Sturla, S.J.1    Kablaoui, N.M.2    Buchwald, S.L.3
  • 135
    • 4344685383 scopus 로고    scopus 로고
    • For an excellent review covering enantio-selective metal-catalyzed cycloisomeriza-tion of 1, 6-and 1, 7-enynes, see
    • For an excellent review covering enantio-selective metal-catalyzed cycloisomeriza-tion of 1, 6-and 1, 7-enynes, see: I.J.S. Fairlamb, Angew. Chem. Int. Ed. 2004, 43, 1048.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1048
    • Fairlamb, I.J.S.1
  • 136
    • 0034680568 scopus 로고    scopus 로고
    • For rhodium-catalyzed enantioselective enyne cycloisomerization and hydrosily-lation-cyclization, see:
    • For rhodium-catalyzed enantioselective enyne cycloisomerization and hydrosily-lation-cyclization, see: C. Ping, X. Zhang, Angew. Chem. Int. Ed. 2000, 39, 4104;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4104
    • Ping, C.1    Zhang, X.2
  • 141
    • 0040196048 scopus 로고    scopus 로고
    • For a biographical sketch of Paul Saba-tier, see:
    • For a biographical sketch of Paul Saba-tier, see: A. Lattes, C. R. Acad. Sci. Ser. IIC: Chemie 2000, 3, 705.
    • (2000) C. R. Acad. Sci. Ser. IIC: Chemie , vol.3 , pp. 705
    • Lattes, A.1
  • 142
    • 3042574588 scopus 로고
    • For a biographical sketch of Roger Adams, see:
    • For a biographical sketch of Roger Adams, see: D.S. Tarbell, A.T. Tarbell, J. Chem. Ed. 1979, 56, 163.
    • (1979) J. Chem. Ed. , vol.56 , pp. 163
    • Tarbell, D.S.1    Tarbell, A.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.