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Volumn 73, Issue 21, 2008, Pages 8422-8436

Palladium- and nickel-catalyzed cross-couplings of unsaturated halides bearing relatively acidic protons with organozinc reagents

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; ATOMS; BEARINGS (STRUCTURAL); CHEMICAL REACTIONS; ELECTRIC POWER PLANTS; NICKEL ALLOYS; ORGANOMETALLICS; PALLADIUM; PROTONS; ZINC;

EID: 55249089203     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015852     Document Type: Article
Times cited : (98)

References (41)
  • 1
    • 0003397781 scopus 로고    scopus 로고
    • 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
  • 3
    • 0003779363 scopus 로고    scopus 로고
    • Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim, Germany
    • (c) Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
    • (1998) Transition Metals for Organic Synthesis
  • 14
    • 1842452582 scopus 로고    scopus 로고
    • For selected examples highlighting the problems with the use of organoboron reagents, see: a
    • For selected examples highlighting the problems with the use of organoboron reagents, see: (a) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2362.
    • (2004) J. Org. Chem , vol.69 , pp. 2362
    • Handy, S.T.1    Zhang, Y.2    Bregman, H.3
  • 21
    • 33748805474 scopus 로고    scopus 로고
    • The preparation of the zinc reagent by transmetalation from the corresponding organomagnesium or organolithium compound led to similar results. For the preperation via direct zinc insertion, see: Krasovskiy, A, Malakhov, V, Gavryushin, A, Knochel, P. Angew. Chem, Int. Ed. 2006, 45, 6040
    • The preparation of the zinc reagent by transmetalation from the corresponding organomagnesium or organolithium compound led to similar results. For the preperation via direct zinc insertion, see: Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040.
  • 26
    • 16844367937 scopus 로고    scopus 로고
    • S-Phos (L3) was purchased from Strem or prepared according to: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
    • S-Phos (L3) was purchased from Strem or prepared according to: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
  • 27
    • 55249084525 scopus 로고    scopus 로고
    • a data see: http:// www.chem.wisc.edu/areas/reich/pkatable/ index.htm and references cited therein.
    • a data see: http:// www.chem.wisc.edu/areas/reich/pkatable/ index.htm and references cited therein.
  • 29
    • 35348925613 scopus 로고    scopus 로고
    • Boros, E. E.; Burova, S. A.; Erickson, G. A; Johns, B. A.; Koble, C. S.; Kurose, N.; Sharp, M. J.; Tabet, E. A.; Thompson, J. B.; Toczko, M. A. Org. Process Res. Dev. 2007, 11, 899.
    • Boros, E. E.; Burova, S. A.; Erickson, G. A; Johns, B. A.; Koble, C. S.; Kurose, N.; Sharp, M. J.; Tabet, E. A.; Thompson, J. B.; Toczko, M. A. Org. Process Res. Dev. 2007, 11, 899.
  • 30
    • 4544311534 scopus 로고    scopus 로고
    • However, for the coupling of 5-bromoindole (7), the zinc reagents 1a, 1g, and 1h had to be prepared by transmetalation from the corresponding magnesium reagents. Control experiments have revealed accelerated cross-coupling reactions in the presence of magnesium salts. For the preparation of organomagnesium reagents, see: (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
    • However, for the coupling of 5-bromoindole (7), the zinc reagents 1a, 1g, and 1h had to be prepared by transmetalation from the corresponding magnesium reagents. Control experiments have revealed accelerated cross-coupling reactions in the presence of magnesium salts. For the preparation of organomagnesium reagents, see: (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
  • 32
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
    • Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
    • (1999) Comprehensive Asymmetric Catalysis
  • 37
    • 55249122769 scopus 로고    scopus 로고
    • 3 (0.07 euro/g) were purchased from Alfa Aesar, L3 (139.50 euro/g) from Strem.
    • 3 (0.07 euro/g) were purchased from Alfa Aesar, L3 (139.50 euro/g) from Strem.
  • 38
    • 0038732070 scopus 로고    scopus 로고
    • For the reactivity of 1,1-bimetallic species towards protonation, see also: Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1043.
    • For the reactivity of 1,1-bimetallic species towards protonation, see also: Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1043.
  • 39
    • 0001049972 scopus 로고
    • For the preparation of zinc and copper organometallics bearing acidic hydrogens, see
    • For the preparation of zinc and copper organometallics bearing acidic hydrogens, see: Knoess, H. P.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1991, 56, 5974.
    • (1991) J. Org. Chem , vol.56 , pp. 5974
    • Knoess, H.P.1    Rozema, M.J.2    Knochel, P.3
  • 40
    • 55249085695 scopus 로고    scopus 로고
    • Using OctZnI·LiCl or PhCH2ZnCl·LiCl led to similar results
    • 2ZnCl·LiCl led to similar results.
  • 41
    • 0004219714 scopus 로고    scopus 로고
    • 2nd ed, Schlosser, M, Ed, Wiley: Chichester, UK
    • Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, UK, 2002.
    • (2002) Organometallics in Synthesis: A Manual


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.