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Volumn , Issue 5, 2008, Pages 774-776

Rhodium-catalyzed hydroarylation and hydroalkenylation of alkynes using organo [2-(hydroxymethyl)phenyl]dimethylsilanes

Author keywords

Addition reaction; Alkyne; Rhodium; Silicon

Indexed keywords

1,2 BIS(DIPHENYLPOSPHINO)BENZENE; 1,3 DIENE DERIVATIVE; ALKADIENE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; ETHYLENE; ORGANO[2 (HYDROXYMETHYL)PHENYL]DIMETHYLSILANE DERIVATIVE; ORGANOMETALLIC COMPOUND; RHODIUM; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

EID: 41349095715     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042812     Document Type: Article
Times cited : (19)

References (41)
  • 7
    • 3042780057 scopus 로고    scopus 로고
    • For rhodium-catalyzed arylation of alkynes followed by intra- and intermolecular trap with electrophiles or another unsaturated bond, see: (a) Lautens, M, Marquardt, T. J. Org. Chem. 2004, 69, 4607
    • For rhodium-catalyzed arylation of alkynes followed by intra- and intermolecular trap with electrophiles or another unsaturated bond, see: (a) Lautens, M.; Marquardt, T. J. Org. Chem. 2004, 69, 4607.
  • 30
    • 19544365278 scopus 로고    scopus 로고
    • For use of organozinc reagents, see: a
    • For use of organozinc reagents, see: (a) Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 2071.
    • (2005) Org. Lett , vol.7 , pp. 2071
    • Shintani, R.1    Hayashi, T.2
  • 33
    • 33751575643 scopus 로고    scopus 로고
    • For rhodium-catalyzed hydrophosphination of alkynes using silylphosphines, see
    • (b) For rhodium-catalyzed hydrophosphination of alkynes using silylphosphines, see: Hayashi, M.; Matsuura, Y.; Watanabe, Y. J. Org. Chem. 2006, 71, 9248.
    • (2006) J. Org. Chem , vol.71 , pp. 9248
    • Hayashi, M.1    Matsuura, Y.2    Watanabe, Y.3
  • 34
    • 34547468353 scopus 로고    scopus 로고
    • For rhodium-catalyzed 1,4-addition reactions using 1, see: (a) Nakao, Y.; Chen, J.; Imanaka, H.; Hiyama, T.; Ichikawa, Y.; Duan, W.-L.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 9137.
    • For rhodium-catalyzed 1,4-addition reactions using 1, see: (a) Nakao, Y.; Chen, J.; Imanaka, H.; Hiyama, T.; Ichikawa, Y.; Duan, W.-L.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 9137.
  • 36
    • 41349087464 scopus 로고    scopus 로고
    • 2 (6.8 mg, 30 μmol Rh) and DPPBz (13.4 mg, 30 μmol) in toluene (1.0 mL) were added 1 (1.50 mmol), 2 (1.00 mmol), and tridecane (an internal standard, 92 mg, 0.50 mmol) sequentially, and the resulting mixture was stirred at 100°C. After the time specified in Table 1, the mixture was filtered through a silica gel pad and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford the corresponding adducts in yields listed in Table 1.
    • 2 (6.8 mg, 30 μmol Rh) and DPPBz (13.4 mg, 30 μmol) in toluene (1.0 mL) were added 1 (1.50 mmol), 2 (1.00 mmol), and tridecane (an internal standard, 92 mg, 0.50 mmol) sequentially, and the resulting mixture was stirred at 100°C. After the time specified in Table 1, the mixture was filtered through a silica gel pad and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford the corresponding adducts in yields listed in Table 1.
  • 37
    • 0000487195 scopus 로고
    • For reviews, see: a, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
    • For reviews, see: (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 763-792.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 763-792
    • Hiyama, T.1    Kusumoto, T.2
  • 39
    • 41349106942 scopus 로고    scopus 로고
    • For hydrosilylation to synthesize 1, see:
    • (c) For hydrosilylation to synthesize 1, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.