An efficient procedure for the synthesis of ortho-trialkylsilylaryl triflates:: Easy access to precursors of functionalized arynes

被引:0
作者
Peña, D
Cobas, A
Pérez, D
Guitián, E [1 ]
机构
[1] Univ Santiago Compostela, Dept Quim Organ, Santiago De Compostela 15706, Spain
[2] CSIC, Unidad Asociada, Santiago De Compostela 15706, Spain
来源
SYNTHESIS-STUTTGART | 2002年 / 10期
关键词
silylation; triflates; arynes; metalations;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
o-Trialkylsilylaryl triflates, which are useful aryne precursors, are prepared from o-bromophenols by an efficient, one-pot procedure involving O-silylation, metal-halogen exchange, O- to C-silyl migration, and entrapment of the phenoxide with triflic anhydride.
引用
收藏
页码:1454 / 1458
页数:5
相关论文
共 26 条
  • [1] Synthesis of triphenylene
    Bergmann, E
    Blum-Bergmann, O
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 1441 - 1442
  • [2] DIRECTED ORTHO METALATION OF SILYLOXYBENZAMIDES - ANION INDUCED O -] C SILICON REARRANGEMENT
    BILLEDEAU, RJ
    SIBI, MP
    SNIECKUS, V
    [J]. TETRAHEDRON LETTERS, 1983, 24 (42) : 4515 - 4518
  • [3] HALOGENATION USING N-HALOGEN COMPOUNDS .1. EFFECT OF AMINES ON ORTHO-BROMINATION OF PHENOLS WITH NBS
    FUJISAKI, S
    EGUCHI, H
    OMURA, A
    OKAMOTO, A
    NISHIDA, A
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (05) : 1576 - 1579
  • [4] Hart H., 1994, CHEM TRIPLE BONDED F, V2, P1017
  • [5] SYNTHESIS AND REARRANGEMENT REACTIONS OF ORTHO-FUNCTIONAL PHENYLLITHIUM AND PHENYL SODIUM DERIVATIVES OF ELEMENT-IVB AND ELEMENT-VB
    HEINICKE, J
    NIETZSCHMANN, E
    TZSCHACH, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 243 (01) : 1 - 8
  • [6] FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS
    HIMESHIMA, Y
    SONODA, T
    KOBAYASHI, H
    [J]. CHEMISTRY LETTERS, 1983, (08) : 1211 - 1214
  • [7] Hoffmann R.W., 1967, DEHYDROBENZENE CYCLO
  • [8] SYNTHETIC APPROACHES TOWARD SPIRO[2,3-DIHYDRO-4H-1-BENZOPYRAN-4,1'-CYCLOHEXAN]-2-ONE DERIVATIVES VIA RADICAL REACTIONS - TOTAL SYNTHESIS OF (+/-)-LYCORAMINE
    ISHIZAKI, M
    OZAKI, K
    KANEMATSU, A
    ISODA, T
    HOSHINO, O
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3877 - 3885
  • [9] BROMOPHLOROGLUCINOLS AND THEIR METHYL ETHERS
    KIEHLMANN, E
    LAUENER, RW
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (02): : 335 - 344
  • [10] A new and efficient hypervalent iodine-benzyne precursor, (phenyl) [o-(trimethylsilyl)phenyl]iodonium triflate:: Generation, trapping reaction, and nature of benzyne
    Kitamura, T
    Yamane, M
    Inoue, K
    Todaka, M
    Fukatsu, N
    Meng, ZH
    Fujiwara, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) : 11674 - 11679