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Volumn 27, Issue 18, 1986, Pages 2007-2010

Transition-metal catalyzed regioselective addition of PhMe2SiBEt3Li and Bu3SnBEt3Li to acetylenic compounds in the presence of methanol

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EID: 0001084467     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)84434-2     Document Type: Article
Times cited : (52)

References (19)
  • 7
    • 0000581968 scopus 로고
    • Beiträge zur Chemie des Bors, 123. (Trimethylsilyl)borate aus Alkoxyboranen und Trimethylsilyllithium
    • (1982) Chemische Berichte , vol.115 , pp. 934
    • Biffar1    Noth2
  • 9
    • 84918484568 scopus 로고    scopus 로고
    • 3Li with allyl bromide (5 equivalents) gave allyldimethyl- phenylsilane in 90% yield along with the recovered starting material (85%).
  • 10
    • 84918484567 scopus 로고    scopus 로고
    • Moderate stability of silylborates to water has been reported. See ref. 2b. The use of acetic acid instead of methanol as a proton source resulted in the formation of a mixture containing the vinylsilane and starting material, 1-dodecyne (1:1).
  • 11
    • 37049097718 scopus 로고
    • Regioselective addition of trimethylstannylcopper?dimethyl sulphide to 1-alkynes: synthesis of ?-substituted 2-(trimethylstannyl)-1-alkenes
    • Similar results have been reported in the reaction of stannylcopper and germylcopper reagents with acetylenic substrates
    • (1983) Journal of the Chemical Society, Chemical Communications , pp. 934
    • Piers1    Chong2
  • 14
    • 84918484566 scopus 로고    scopus 로고
    • We are grateful to Toyo Stauffer Chemical Co. for the gift of triethylborane.
  • 15
    • 84918484565 scopus 로고    scopus 로고
    • 3Li. See ref. 2a.
  • 16
    • 84918484564 scopus 로고    scopus 로고
    • The reaction proceeded easily even in the presence of a large excess of methanol (100 equivalents).
  • 17
    • 84918484563 scopus 로고    scopus 로고
    • 4) δ0.34 (s, 6H), 2.33 (t, J = 6.0 Hz, 2H), 3.30 (t, J = 6.0 Hz, 2H), 4.26 (s, 2H), 5.39 (m, 1H), 5.67 (m, 1H), 7.05–7.45 (m, 10H).
  • 18
    • 84918484562 scopus 로고    scopus 로고
    • In contrast, silylboration did not proceed at all in the absence of transition-metal catalysts.
  • 19
    • 84918484561 scopus 로고    scopus 로고
    • Financial support by the Ministry of Education, Science, and Culture, Japanese Government (Grant-in-aid for Special Project Research ♯60219015) is acknowledged.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.