Nickel(BiPhePhos)-Catalyzed Hydrocyanation of Styrene-Highly Increased Catalytic Activity by Optimized Operational Procedures

被引:0
作者
Koehler, Till [1 ]
Rienhoff, Bernd [1 ]
Vogt, Dieter [1 ]
机构
[1] TU Dortmund, Dept Bioand Chem Engn, Chair Ind Chem, Emil-Figge-Str 68, D-44227 Dortmund, Germany
关键词
hydrocyanation; activity enhancement; BiPhePhos; homogeneous catalysis; nickel; hydrogen cyanide; NICKEL(0); LIGANDS; COMPLEXES; OLEFINS; ALKENES;
D O I
10.3390/catal14030210
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Nitriles are versatile and highly desired chemical intermediates for a range of products. Their economic large-scale production requires highly efficient and selective synthesis. The nickel-catalyzed hydrocyanation of C=C double bonds provides such selective and 100% atom-economical access to nitriles, but the catalysts hitherto lack activity and longevity. Yet, the literature focusing on increased catalytic activity or optimized operational procedures is scarce, at the least. Here, we present a thorough investigation and optimization of operational procedures using a commercially available diphosphite ligand and styrene as a model substrate. This led us to achieve a TOF20 of more than 300,000 h-1.
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页数:11
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共 23 条
  • [1] Anastas PT, 1998, GREEN CHEMISTRY, P1
  • [2] CHELATING DIPHOSPHITE COMPLEXES OF NICKEL(0) AND PLATINUM(0) - THEIR REMARKABLE STABILITY AND HYDROCYANATION ACTIVITY
    BAKER, MJ
    HARRISON, KN
    ORPEN, AG
    PRINGLE, PG
    SHAW, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) : 803 - 804
  • [3] Billig E., 1988, U.S. Patent, Patent No. [12,329, 12329]
  • [4] Ligand development in the Ni-catalyzed hydrocyanation of alkenes
    Bini, Laura
    Muller, Christian
    Vogt, Dieter
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (44) : 8325 - 8334
  • [5] Mechanistic Studies on Hydrocyanation Reactions
    Bini, Laura
    Muller, Christian
    Vogt, Dieter
    [J]. CHEMCATCHEM, 2010, 2 (06) : 590 - 608
  • [6] Bohnet M., 2003, Ullmanns Encyclopedia of Industrial Chemistry, V6th, DOI [10.1002/14356007, DOI 10.1002/14356007]
  • [7] Enantioselective Nickel-Catalyzed Hydrocyanation of Vinylarenes Using Chiral Phosphine-Phosphite Ligands and TMS-CN as a Source of HCN
    Falk, Anna
    Goederz, Anna-Lena
    Schmalz, Hans-Guenther
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1576 - 1580
  • [8] ORGANIC CHEMISTRY Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation
    Fang, Xianjie
    Yu, Peng
    Morandi, Bill
    [J]. SCIENCE, 2016, 351 (6275) : 832 - 836
  • [9] Fazekas E., 2018, Ph.D. Thesis
  • [10] Ni-Catalyzed Isomerization-Hydrocyanation Tandem Reactions: Access to Linear Nitriles from Aliphatic Internal Olefins
    Gao, Jihui
    Ni, Jie
    Yu, Rongrong
    Cheng, Gui-Juan
    Fang, Xianjie
    [J]. ORGANIC LETTERS, 2021, 23 (02) : 486 - 490