Hydrosilylation of nitriles and tertiary amides using a zinc precursor

被引:3
作者
Kumar, Ravi [1 ]
Meher, Rohan Kumar [1 ]
Karmakar, Himadri [1 ]
Panda, Tarun K. [1 ]
机构
[1] Indian Inst Technol Hyderabad, Dept Chem, Sangareddy 502284, Telangana, India
关键词
CATALYTIC HYDROSILYLATION; REDUCTION; KETONES; HYDRIDE; IMINES; REACTIVITY; COMPLEXES; EFFICIENT; SECONDARY; ENAMINES;
D O I
10.1039/d4ob00161c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a competent and selective hydrosilylation of nitriles and tertiary amides catalyzed by the readily available zinc bis(hexamethyldisilazide) under solvent-free and mild conditions, making it a sustainable and desirable alternative to existing methods. Both protocols afforded high conversion, superior selectivity, and a broad substrate scope, from electron-withdrawing to electron-donating and heterocyclic substitutions. A competent and selective hydrosilylation of nitriles and tertiary amides catalyzed by zinc bis(hexamethyldisilazide) [Zn(HMDS)2] under solvent-free and mild conditions are reported, as a sustainable and desirable alternative to existing methods.
引用
收藏
页码:3053 / 3058
页数:6
相关论文
共 48 条
  • [1] Unexpected Role of Zinc Hydride in Catalytic Hydrosilylation of Ketones and Nitriles
    Boone, Courtney
    Korobkov, Ilia
    Nikonov, Georgii I.
    [J]. ACS CATALYSIS, 2013, 3 (10): : 2336 - 2340
  • [2] Synthesis of functionalised fluorescent dyes and their coupling to amines and amino acids
    Briggs, MSJ
    Bruce, I
    Miller, JN
    Moody, CJ
    Simmonds, AC
    Swann, E
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (07): : 1051 - 1058
  • [3] Metal-Free Reduction of Secondary and Tertiary N-Phenyl Amides by Tris(pentafluorophenyl)boron-Catalyzed Hydrosilylation
    Chadwick, Ryan C.
    Kardelis, Vladimir
    Lim, Philip
    Adronov, Alex
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) : 7728 - 7733
  • [4] Cationic Zinc Hydride Catalyzed Carbon Dioxide Reduction to Formate: Deciphering Elementary Reactions, Isolation of Intermediates, and Computational Investigations
    Chambenahalli, Raju
    Bhargav, R. M.
    McCabe, Karl N.
    Andrews, Alex P.
    Ritter, Florian
    Okuda, Jun
    Maron, Laurent
    Venugopal, Ajay
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (26) : 7391 - 7401
  • [5] Base-Catalyzed Hydrosilylation of Nitriles to Amines and Esters to Alcohols
    Clarke, Joshua A.
    van der Est, Art
    Nikonov, Georgii, I
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (31) : 4434 - 4439
  • [6] Lisdexamfetamine for Treatment of Attention-Deficit/Hyperactivity Disorder
    Cowles, Brian J.
    [J]. ANNALS OF PHARMACOTHERAPY, 2009, 43 (04) : 669 - 676
  • [7] Zinc-Catalyzed Chemoselective Reduction of Tertiary and Secondary Amides to Amines
    Das, Shoubhik
    Addis, Daniele
    Junge, Kathrin
    Beller, Matthias
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (43) : 12186 - 12192
  • [8] Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance
    Das, Shoubhik
    Addis, Daniele
    Zhou, Shaolin
    Junge, Kathrin
    Beller, Matthias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 1770 - +
  • [9] Bridging vs. Chelating Coordination Modes of Vinylsilanes in CuI π-Complexes: Structure and Stability
    Duzak, Tomasz
    Zarychta, Bartosz
    Olijnyk, Volodymyr
    [J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2014, 640 (01): : 57 - 62
  • [10] Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines
    Gandhamsetty, Narasimhulu
    Jeong, Jinseong
    Park, Juhyeon
    Park, Sehoon
    Chang, Sukbok
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14) : 7281 - 7287