메뉴 건너뛰기




Volumn 16, Issue 30, 2010, Pages 9193-9202

The nickel-catalyzed carbonylative cycloaddition of allyl halides and acetylenes: An efficient tool for cyclopentane annelation

Author keywords

Carbonylation; Catalysis; Cycloaddition; Iron; Nickel

Indexed keywords

ALLYL HALIDES; AMINE MOIETIES; DIMERIC SPECIES; ELECTRONIC EFFECTS; GOOD YIELD; HIGH YIELD; IRON-NICKEL; REDUCTANTS; STRAIGHT-FORWARD METHOD;

EID: 77955448573     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903273     Document Type: Article
Times cited : (10)

References (61)
  • 3
    • 68049140888 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3168-3210
  • 5
    • 18844403627 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3022-3037;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3022-3037
  • 7
    • 0038665161 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1800-1810;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1800-1810
  • 9
    • 84890780346 scopus 로고    scopus 로고
    • Ed.: P. A. Evans, Wiley-VCH, Weinheim
    • N. Jeong in Modern Rhodium-Catalyzed Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, pp. 215-240;
    • (2005) Modern Rhodium-Catalyzed Reactions , pp. 215-240
    • Jeong, N.1
  • 29
    • 77955453775 scopus 로고    scopus 로고
    • We tried other bases: Calcium carbonate was not as efficient as sodium acetate and proton scavengers tertiary amines, proton sponge, or 2, 3-dimethylbut-2-ene either inhibited the reaction completely, giving a strong blue color amines, and/or gave very small yields of the adduct
    • We tried other bases: Calcium carbonate was not as efficient as sodium acetate and proton scavengers (tertiary amines, proton sponge, or 2, 3-dimethylbut-2-ene) either inhibited the reaction completely, giving a strong blue color (amines), and/or gave very small yields of the adduct.
  • 37
    • 77955452899 scopus 로고    scopus 로고
    • The extreme purity of the cycloadduct obtained with this reductant is remarkable. At the end of the four cycles an insoluble red precipitate was formed, whereas the supernatant was colorless and CO uptake was definitely stopped. Plausibly, the resulting tetraaminodicarbenium dihalide trapped the degraded NiII in an insoluble polymeric cationic complex, although this has not been further investigated
    • The extreme purity of the cycloadduct obtained with this reductant is remarkable. At the end of the four cycles an insoluble red precipitate was formed, whereas the supernatant was colorless and CO uptake was definitely stopped. Plausibly, the resulting tetraaminodicarbenium dihalide trapped the degraded NiII in an insoluble polymeric cationic complex, although this has not been further investigated.
  • 38
    • 77955434148 scopus 로고    scopus 로고
    • 5 formation
    • 5] formation).
  • 41
    • 77955434316 scopus 로고    scopus 로고
    • The attempted esterification of the crude product with methanol at reflux and a catalytic amount of p-toluenesulfonic acid led again to 3a. All attempts to silylate, methylate, or acylate the hydroxy functionality also failed
    • The attempted esterification of the crude product with methanol at reflux and a catalytic amount of p-toluenesulfonic acid led again to 3a. All attempts to silylate, methylate, or acylate the hydroxy functionality also failed.
  • 42
    • 77955435867 scopus 로고
    • Iodine is known to catalyze the condensation of acetone to diacetone alcohol
    • Iodine is known to catalyze the condensation of acetone to diacetone alcohol: J. B. Conant, N. Tuttle, Org. Synth. 1921, 1, 53.
    • (1921) Org. Synth , vol.1 , pp. 53
    • Conant, J.B.1    Tuttle, N.2
  • 47
    • 77955436842 scopus 로고    scopus 로고
    • Although almost all the spectral data and chemical behavior is indicative of this structure, one of the referees disagrees with us
    • Although almost all the spectral data and chemical behavior is indicative of this structure, one of the referees disagrees with us.
  • 48
    • 77955440727 scopus 로고    scopus 로고
    • 13C NMR experiment showed no significant differences in the spectrum
    • 13C NMR experiment showed no significant differences in the spectrum.
  • 50
    • 77955435370 scopus 로고    scopus 로고
    • an experiment performed under carbonylative conditions in the absence of the nickel salt gave only 1, 5-hexadiene; c
    • an experiment performed under carbonylative conditions in the absence of the nickel salt gave only 1, 5-hexadiene; c)
  • 52
    • 0001478826 scopus 로고
    • Ed.: B. M. Trost, I. Fleming, Pergamon Press, Oxford
    • Comprehensive Organic Synthesis, Vol. 2 (Ed.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 723-726.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 723-726
  • 53
    • 77955465050 scopus 로고
    • I oxidation state. a, Ed.: R. B. King, Wiley, New York
    • I oxidation state. a) Encyclopedia of Inorganic Chemistry, Vol. 5 (Ed.: R. B. King), 1995, Wiley, New York, pp. 2386-2388
    • (1995) Encyclopedia of Inorganic Chemistry , vol.5 , pp. 2386-2388
  • 54
    • 77955462722 scopus 로고
    • Ed.: R. B. King, Wiley, New York
    • and Encyclopedia of Inorganic Chemistry, Vol. 5 (Ed.: R. B. King), 1995, Wiley, New York, pp. 2416-2419;
    • (1995) Encyclopedia of Inorganic Chemistry , vol.5 , pp. 2416-2419
  • 58
    • 77955456784 scopus 로고    scopus 로고
    • Unlike externally added alcohols, an alkynol can coordinate the active metal center, its distal hydroxy functionality approaching the appropriate intermediate. Hence a high yield of the ester may arise
    • Unlike externally added alcohols, an alkynol can coordinate the active metal center, its distal hydroxy functionality approaching the appropriate intermediate. Hence a high yield of the ester may arise.
  • 59
    • 77955460928 scopus 로고    scopus 로고
    • Plain unconjugated olefins like 1, 5-hexadiene do not undergo the carbonylative cycloaddition reaction with allyl halides. Electrophilic attack of an allylic iron halide by allyl halide would result in the release of uncoordinated 1, 5-hexadiene
    • Plain unconjugated olefins like 1, 5-hexadiene do not undergo the carbonylative cycloaddition reaction with allyl halides. Electrophilic attack of an allylic iron halide by allyl halide would result in the release of uncoordinated 1, 5-hexadiene.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.