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Volumn 27, Issue 20, 2008, Pages 5390-5393

Counteranion-accelerated RhiOAc-catalyzed regioselective hydroboration of vinylarenes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC ACTIVITIES; HYDROBORATION; PINACOLBORANE; REGIOSELECTIVE; VINYLARENES;

EID: 55249093448     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800465q     Document Type: Article
Times cited : (25)

References (36)
  • 1
    • 0004225917 scopus 로고    scopus 로고
    • Jacoosen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: New York
    • (a) Hayashi, I. In Comprehensive Asymmetric Catalysis; Jacoosen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 1, p 349.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 349
    • Hayashi, I.1
  • 3
    • 0000878323 scopus 로고    scopus 로고
    • Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359.
    • (c) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359.
  • 20
    • 55249084804 scopus 로고    scopus 로고
    • The screening of ligands clarified the notion that DPPB is suitable for the regioselectivity in the present catalysis. Other ligands diminished the regioselectivity in some cases: see the Supporting Information
    • The screening of ligands clarified the notion that DPPB is suitable for the regioselectivity in the present catalysis. Other ligands diminished the regioselectivity in some cases: see the Supporting Information.
  • 21
    • 0000644870 scopus 로고    scopus 로고
    • 2 in pinacolborane was suggested by: Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168-2171.
    • 2 in pinacolborane was suggested by: Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168-2171.
  • 25
    • 0345356309 scopus 로고    scopus 로고
    • The use of catecholborane (HBcat) under the same reaction conditions as entry 5, Table 1 gave a mixture of 1-phenylethanol and 2-phenylethanol in 82% yield with 93/7 ratio after the oxidation of the crude boronate compounds. The preceding reports detailed the difference between HBpin and HBcat; see ref 3i and: Lam, W. H, Shimada, S, Batsanov, A. S, Lin, Z, Marder, T. B, Cowan, J. A, Howard, J. A. K, Mason, S. A, McIntyre, G. J. Organometallics 2003, 22, 4557-4568. A mechanistic investigation will be carried out in due course in future studies
    • The use of catecholborane (HBcat) under the same reaction conditions as entry 5, Table 1 gave a mixture of 1-phenylethanol and 2-phenylethanol in 82% yield with 93/7 ratio after the oxidation of the crude boronate compounds. The preceding reports detailed the difference between HBpin and HBcat; see ref 3i and: Lam, W. H.; Shimada, S.; Batsanov, A. S.; Lin, Z.; Marder, T. B.; Cowan, J. A.; Howard, J. A. K.; Mason, S. A.; McIntyre, G. J. Organometallics 2003, 22, 4557-4568. A mechanistic investigation will be carried out in due course in future studies.
  • 26
    • 55249083649 scopus 로고    scopus 로고
    • The reaction in the presence of low catalyst loading should be conducted under precisely dehydrated conditions; the decomposition of HBpin with H 2O causes decreasing regioselectivity
    • 2O causes decreasing regioselectivity.
  • 29
    • 55249100882 scopus 로고    scopus 로고
    • Other counteranions, such as pivalate and benzoate, gave similar results
    • Other counteranions, such as pivalate and benzoate, gave similar results.
  • 30
    • 55249086862 scopus 로고    scopus 로고
    • The reaction in DMSO as a solvent gave better results in some cases. The details are described in the Supporting Information
    • The reaction in DMSO as a solvent gave better results in some cases. The details are described in the Supporting Information.
  • 31
    • 55249120335 scopus 로고    scopus 로고
    • The reaction of a 1,1-disubstituted ethylene, such as a-methylstyrene, gave a mixture of regioisomers. We have not examined the reaction of trisubstituted ethylenes due to insufficient regioselectivity
    • The reaction of a 1,1-disubstituted ethylene, such as a-methylstyrene, gave a mixture of regioisomers. We have not examined the reaction of trisubstituted ethylenes due to insufficient regioselectivity.
  • 32
    • 55249091260 scopus 로고    scopus 로고
    • 31P NMR experiments were examined; however, the precise characterization of the Rh(III) intermediate is difficult. Details of the NMR experiments are described in the Supporting Information. Further investigation is ongoing to clarify Rh(III) intermediates.
    • 31P NMR experiments were examined; however, the precise characterization of the Rh(III) intermediate is difficult. Details of the NMR experiments are described in the Supporting Information. Further investigation is ongoing to clarify Rh(III) intermediates.
  • 34
    • 55249101117 scopus 로고    scopus 로고
    • Iacac did not promote the reaction at all (entry 3, Table 1). In addition, the distilled HBpin can promote the present reaction. The generation of a borate-Rh(I) complex does not seem to be essential.
    • Iacac did not promote the reaction at all (entry 3, Table 1). In addition, the distilled HBpin can promote the present reaction. The generation of a borate-Rh(I) complex does not seem to be essential.
  • 36
    • 0037042235 scopus 로고    scopus 로고
    • 2 Hayashi, T.; Takahashi, M.; Takaya. Y.; Ogasawara, M. J. Am. Chem. Soc. 2002. 124, 5052-5058.
    • 2 Hayashi, T.; Takahashi, M.; Takaya. Y.; Ogasawara, M. J. Am. Chem. Soc. 2002. 124, 5052-5058.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.