Iron-Catalyzed Cross-Coupling of Alkyl Sulfonates with Arylzinc Reagents

被引:76
作者
Ito, Shingo
Fujiwara, Yu-ichi
Nakamura, Eiichi
Nakamura, Masaharu [1 ]
机构
[1] Kyoto Univ, IRCELS, Inst Chem Res, Grad Sch Engn, Kyoto 6110011, Japan
关键词
GRIGNARD-REAGENTS; FUNCTIONALIZED ARYLMAGNESIUM; LITHIUM DIORGANOCUPRATES(I); HALIDES; TOSYLATES; NICKEL; STEREOCHEMISTRY; ALKENYLATION; ARYLATION; BROMIDES;
D O I
10.1021/ol901610a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly in the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI2. The in situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.
引用
收藏
页码:4306 / 4309
页数:4
相关论文
共 60 条
  • [1] Recent Advances in Iron Catalysis in Organic Synthesis
    Bauer, Eike B.
    [J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (16) : 1341 - 1369
  • [2] Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents
    Bedford, RB
    Betham, M
    Bruce, DW
    Davis, SA
    Frost, RM
    Hird, M
    [J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1398 - 1400
  • [3] Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents
    Bedford, RB
    Betham, M
    Bruce, DW
    Danopoulos, AA
    Frost, RM
    Hird, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) : 1104 - 1110
  • [4] Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens
    Bedford, RB
    Bruce, DW
    Frost, RM
    Goodby, JW
    Hird, M
    [J]. CHEMICAL COMMUNICATIONS, 2004, (24) : 2822 - 2823
  • [5] Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens
    Bedford, RB
    Bruce, DW
    Frost, RM
    Hird, M
    [J]. CHEMICAL COMMUNICATIONS, 2005, (33) : 4161 - 4163
  • [6] Iron-catalysed Negishi coupling of benzyl halides and phosphates
    Bedford, Robin B.
    Huwe, Michael
    Wilkinson, Mark C.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (05) : 600 - 602
  • [7] beta-silyl diorganozinc compounds - A new class of useful zinc reagents
    Berger, S
    Langer, F
    Lutz, C
    Knochel, P
    Mobley, TA
    Reddy, CK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1496 - 1498
  • [8] New copper chemistry .27. beta-silyl organocuprates: The grail of organocuprate chemistry?
    Bertz, SH
    Eriksson, M
    Miao, GB
    Snyder, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) : 10906 - 10907
  • [9] An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides
    Bica, K
    Gaertner, P
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 733 - 735
  • [10] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254