Radical Addition of Silanes to Alkenes Followed by Oxidation

被引:5
作者
Palframan, Matthew J. [1 ]
Parsons, Andrew F. [1 ]
Johnson, Paul [2 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] AstraZeneca, Macclesfield SK10 4TF, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
addition reaction; alcohol; alkene; radical reaction; silane; SILYLATED CYCLOHEXADIENES; SILAFUNCTIONAL COMPOUNDS; CHAIN HYDROSILYLATION; ORGANIC-SYNTHESIS; PETERSON REACTION; CYCLIZATION; BONDS; AGENT;
D O I
10.1055/s-0031-1289568
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenyldimethylsilane and trichlorosilane are shown to undergo efficient radical hydrosilylation reactions, on reaction with various alkenes, using triethylborane as the initiator. Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in good yields. This two-step process leads to the anti-Markovnikov hydration of alkenes.
引用
收藏
页码:2811 / 2814
页数:4
相关论文
共 26 条
  • [1] AGER DJ, 1984, SYNTHESIS-STUTTGART, P384
  • [2] Amrein S, 2002, HELV CHIM ACTA, V85, P3559, DOI 10.1002/1522-2675(200210)85:10<3559::AID-HLCA3559>3.0.CO
  • [3] 2-6
  • [4] Intramolecular radical hydrosilylation -: the first radical 5-endo-dig cyclisation
    Amrein, S
    Studer, A
    [J]. CHEMICAL COMMUNICATIONS, 2002, (15) : 1592 - 1593
  • [5] Radical transfer hydrosilylation/cyclization using silylated cyclohexadienes
    Amrein, S
    Timmermann, A
    Studer, A
    [J]. ORGANIC LETTERS, 2001, 3 (15) : 2357 - 2360
  • [6] Barbero A, 2000, SYNTHESIS-STUTTGART, P1223
  • [7] Intramolecular radical-chain hydrosilylation catalysed by thiols: cyclisation of alkenyloxysilanes
    Cai, YD
    Roberts, BP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 467 - 475
  • [8] TRIS(TRIMETHYLSILYL)SILANE - A NEW REDUCING AGENT
    CHATGILIALOGLU, C
    GRILLER, D
    LESAGE, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3641 - 3642
  • [9] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED HYDROXY GROUP
    FLEMING, I
    HENNING, R
    PARKER, DC
    PLAUT, HE
    SANDERSON, PEJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04): : 317 - 337
  • [10] Enantioselective radical-chain hydrosilylation of prochiral alkenes using optically active thiol catalysts
    Haque, MB
    Roberts, BP
    [J]. TETRAHEDRON LETTERS, 1996, 37 (50) : 9123 - 9126