Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes

被引：237
|
作者：
Wu, Jessica Y. [1 ]
Moreau, Benoit [1 ]
Ritter, Tobias [1 ]
机构：
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 36期
关键词：
TRANSITION-METAL-COMPLEXES; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; ALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; LIGANDS; CYCLOISOMERIZATION; HYDROBORATIONS; CATECHOLBORANE; ALLYLBORATION;
D O I：
10.1021/ja9048493
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords gamma-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.
引用
收藏
页码：12915 / +
页数：4
相关论文
共 50 条
  • [41] 1,4-Functionalization of 1,3-Dienes With Low-Valent Iron Catalysts
    McNeill, Eric
    Ritter, Tobias
    ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (08) : 2330 - 2343
  • [42] Iron-Catalyzed Vinylsilane Dimerization and Cross-Cycloadditions with 1,3-Dienes: Probing the Origins of Chemo- and Regioselectivity
    Kennedy, C. Rose
    Joannou, Matthew, V
    Steves, Janelle E.
    Hoyt, Jordan M.
    Kovel, Carli B.
    Chirik, Paul J.
    ACS CATALYSIS, 2021, 11 (03): : 1368 - 1379
  • [43] Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes
    Braconi, Elena
    Gotzinger, Alissa C.
    Cramer, Nicolai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (47) : 19819 - 19824
  • [44] REACTIVITY OF PHOSPHENIUM IONS TOWARD 1,3-DIENES AND 1,4-DIENES
    COWLEY, AH
    KEMP, RA
    LASCH, JG
    NORMAN, NC
    STEWART, CA
    WHITTLESEY, BR
    WRIGHT, TC
    INORGANIC CHEMISTRY, 1986, 25 (06) : 740 - 749
  • [45] CODIMERIZATION MECHANISM OF 1,3-DIENES WITH METHYL ACRYLATE, CATALYZED BY IRON COMPLEXES
    TOLSTIKOV, GA
    DZHEMILEV, UM
    KHUSNUTDINOV, RI
    ZHURNAL ORGANICHESKOI KHIMII, 1979, 15 (04): : 694 - 698
  • [46] Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes
    Tamang, Sem Raj
    Singh, Arpita
    Unruh, Daniel K.
    Findlater, Michael
    ACS CATALYSIS, 2018, 8 (07): : 6186 - 6191
  • [47] MECHANISM OF 1,4-CYCLOADDITION OF DICHLOROGERMYLENE TO 1,3-DIENES
    KOLESNIKOV, SP
    IOFFE, AI
    NEFEDOV, OM
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (04): : 896 - 896
  • [48] STEREOCONTROLLED APPROACH TO 1,4-DISUBSTITUTED 1,3-DIENES
    TROST, BM
    GODLESKI, SA
    IPPEN, J
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (24): : 4559 - 4564
  • [49] TRIS(ACETONITRILE)TRICARBONYLCHROMIUM(0) CATALYZED 1,4-ADDITION OF HYDROGEN TO 1,3-DIENES
    SCHROEDER, MA
    WRIGHTON, MS
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 74 (02) : C29 - C32
  • [50] Copper-Catalyzed Highly Enantioselective 1,4-Protoboration of Terminal 1,3-Dienes
    Guan, Qitao
    Ji, Yuqi
    Zhao, Qian
    Zhang, Chun
    CCS CHEMISTRY, 2022, 4 (05): : 1545 - 1556
12345