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Volumn 41, Issue 31, 2000, Pages 5877-5880

Regio- and stereoselective synthesis of allylboranes via platinum(0)- catalyzed borylation of allyl halides with pinacolborane

Author keywords

Allyl halides; Allylborane; Coupling reactions; Pinacolborane; Platinum catalyst

Indexed keywords

BORANE DERIVATIVE; HALIDE;

EID: 0034729977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00881-9     Document Type: Article
Times cited : (46)

References (23)
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    • For examples, see: (a)
    • For examples, see: (a) Schlosser, M.; Rauchschwalb, G. J. Am. Chem. Soc. 1978, 100, 3258. (b) Brown, H. C.; DeLue, N. R.; Yamamoto, Y.; Maruyama, K.; Kasahara, T.; Murahashi, S.-I. J. Org. Chem. 1977, 42, 4088. (c) Watanabe, T.; Miyaura, N.; Suzuki, A. J. Organomet. Chem. 1993, 444, C1.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3258
    • Schlosser, M.1    Rauchschwalb, G.2
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    • 0002734851 scopus 로고
    • (c)
    • For examples, see: (a) Schlosser, M.; Rauchschwalb, G. J. Am. Chem. Soc. 1978, 100, 3258. (b) Brown, H. C.; DeLue, N. R.; Yamamoto, Y.; Maruyama, K.; Kasahara, T.; Murahashi, S.-I. J. Org. Chem. 1977, 42, 4088. (c) Watanabe, T.; Miyaura, N.; Suzuki, A. J. Organomet. Chem. 1993, 444, C1.
    • (1993) J. Organomet. Chem. , vol.444
    • Watanabe, T.1    Miyaura, N.2    Suzuki, A.3
  • 15
    • 0000856485 scopus 로고
    • For the palladium-catalyzed reduction of organic halides, see: (a)
    • For the palladium-catalyzed reduction of organic halides, see: (a) Egli, R. A. Helv. Chim. Acta 1968, 51, 2090. (b) Hutchins, R. O.; Learn, K. J. Org. Chem. 1982, 47, 4380. (c) Lipshutz, B. H.; Buzard, D. J.; Vivian, R. W. Tetrahedron Lett. 1999, 40, 6871.
    • (1968) Helv. Chim. Acta , vol.51 , pp. 2090
    • Egli, R.A.1
  • 16
    • 33845554413 scopus 로고
    • (b)
    • For the palladium-catalyzed reduction of organic halides, see: (a) Egli, R. A. Helv. Chim. Acta 1968, 51, 2090. (b) Hutchins, R. O.; Learn, K. J. Org. Chem. 1982, 47, 4380. (c) Lipshutz, B. H.; Buzard, D. J.; Vivian, R. W. Tetrahedron Lett. 1999, 40, 6871.
    • (1982) J. Org. Chem. , vol.47 , pp. 4380
    • Hutchins, R.O.1    Learn, K.2
  • 17
    • 0033578622 scopus 로고    scopus 로고
    • (c)
    • For the palladium-catalyzed reduction of organic halides, see: (a) Egli, R. A. Helv. Chim. Acta 1968, 51, 2090. (b) Hutchins, R. O.; Learn, K. J. Org. Chem. 1982, 47, 4380. (c) Lipshutz, B. H.; Buzard, D. J.; Vivian, R. W. Tetrahedron Lett. 1999, 40, 6871.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6871
    • Lipshutz, B.H.1    Buzard, D.J.2    Vivian, R.W.3
  • 18
    • 85037952138 scopus 로고    scopus 로고
    • 4. The solvent was evaporated, and product 3 was isolated by distillation with Kugelrohr
    • 4. The solvent was evaporated, and product 3 was isolated by distillation with Kugelrohr.
  • 19
    • 85037968965 scopus 로고    scopus 로고
    • Under the present conditions, the borylation of cinnamyl acetate gave only 21% yield of 3a along with 4a (23%) and 4a′ (6%)
    • Under the present conditions, the borylation of cinnamyl acetate gave only 21% yield of 3a along with 4a (23%) and 4a′ (6%).
  • 23
    • 85037965101 scopus 로고    scopus 로고
    • 3N (0.25 mmol) in toluene (1 ml) was stirred at 50°C for 16 h. GLC analysis of the reaction mixture indicated formation of the corresponding 3b
    • 3N (0.25 mmol) in toluene (1 ml) was stirred at 50°C for 16 h. GLC analysis of the reaction mixture indicated formation of the corresponding 3b.


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