Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran E and Other Targets of Interest

被引:90
作者
Blaisdell, Thomas P. [1 ]
Morken, James P. [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
关键词
SECONDARY; DIBORATION; OXIDATION; ACTIVATION; RETENTION; INVERSION; ALCOHOLS; ESTERS;
D O I
10.1021/jacs.5b05477
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A hydroxyl functional group positioned beta to a pinacol boronate can serve to direct palladium-catalyzed cross-coupling reactions. This feature can be used to control the reaction site in multiply borylated substrates and can activate boronates for reaction that would otherwise be unreactive.
引用
收藏
页码:8712 / 8715
页数:4
相关论文
共 35 条
  • [31] TAMARU Y, 1979, TETRAHEDRON LETT, P1401
  • [32] OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS BY THE CATALYSIS OF PALLADIUM
    TAMARU, Y
    YAMADA, Y
    INOUE, K
    YAMAMOTO, Y
    YOSHIDA, Z
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) : 1286 - 1292
  • [33] Ruphos-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates
    van den Hoogenband, Adri
    Lange, Jos H. M.
    Terpstra, Jan Willem
    Koch, Melle
    Visser, Gerben M.
    Visser, Martin
    Korstanje, Ties J.
    Jastrzebski, Johann T. B. H.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (26) : 4122 - 4124
  • [34] Chemistry of sponges.: 19.: Novel bioactive metabolites from Hamigera tarangaensis
    Wellington, KD
    Cambie, RC
    Rutledge, PS
    Bergquist, PR
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (01): : 79 - 85
  • [35] GEMINAL ORGANOMETALLIC COMPOUNDS .I. SYNTHESIS AND STRUCTURE OF 1,1-DIBOROHEXANE
    ZWEIFEL, G
    ARZOUMAN.H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) : 291 - &