Pd-Catalyzed Conjunctive Cross -Coupling between Grignard-Derived Boron "Ate" Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

被引:104
作者
Lovinger, Gabriel J. [1 ]
Aparece, Mark D. [1 ]
Morken, James P. [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
关键词
BORANE INTRAMOLECULAR COMPLEXES; PHASE-TRANSFER CONDITIONS; LITHIATION-BORYLATION; CHIRAL ORGANOBORANES; ASYMMETRIC-SYNTHESIS; HECK REACTIONS; PALLADIUM; ESTERS; ARYL; MIGRATION;
D O I
10.1021/jacs.6b12663
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic enantioselective conjunctive cross couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables "ate" complex formation and overcomes catalytic inhibition by halide ions.
引用
收藏
页码:3153 / 3160
页数:8
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共 77 条
  • [1] Toward an understanding of the factors responsible for the 1,2-migration of alkyl groups in borate complexes
    Aggarwal, VK
    Fang, GY
    Ginesta, X
    Howells, DM
    Zaja, M
    [J]. PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 215 - 229
  • [2] EVIDENCE FOR THE LIGATION OF PALLADIUM(0) COMPLEXES BY ACETATE IONS - CONSEQUENCES ON THE MECHANISM OF THEIR OXIDATIVE ADDITION WITH PHENYL IODIDE AND PHPD(OAC)(PPH(3))(2) AS INTERMEDIATE IN THE HECK REACTION
    AMATORE, C
    CARRE, E
    JUTAND, A
    MBARKI, MA
    MEYER, G
    [J]. ORGANOMETALLICS, 1995, 14 (12) : 5605 - 5614
  • [3] Rate and mechanism of the heck reactions of arylpalladium complexes ligated by a bidentate P,P ligand with an electron-rich alkene (isobutyl vinyl ether)
    Amatore, Christian
    Godin, Beatrice
    Jutand, Anny
    Lemaitre, Frederic
    [J]. ORGANOMETALLICS, 2007, 26 (07) : 1757 - 1761
  • [4] Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate PP ligand in Heck reactions
    Amatore, Christian
    Godin, Beatrice
    Jutand, Anny
    Lemaitre, Frederic
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) : 2002 - 2011
  • [5] REGIOSELECTIVE PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS WITH 4-NITROPHENYL TRIFLATE - CONTROL BY ADDITION OF HALIDE-IONS
    ANDERSSON, CM
    HALLBERG, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) : 2112 - 2114
  • [6] PALLADIUM-CATALYZED ARYLATION OF SILOXYCYCLOPROPANES WITH ARYL TRIFLATES - CARBON CHAIN ELONGATION VIA CATALYTIC CARBON CARBON BOND-CLEAVAGE
    AOKI, S
    FUJIMURA, T
    NAKAMURA, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) : 3296 - 3298
  • [7] Stereodivergent Olefination of Enantioenriched Boronic Esters
    Armstrong, Roly J.
    Garcia-Ruiz, Cristina
    Myers, Eddie L.
    Aggarwal, Varinder K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (03) : 786 - 790
  • [8] Progress and developments in the turbo Grignard reagent i-PrMgCl•LiCl: a ten-year journey
    Bao, Robert Li-Yuan
    Zhao, Rong
    Shi, Lei
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (32) : 6884 - 6900
  • [9] Barl N. M., 2014, HETEROCYCLES, V88, P827