Manganese Catalyzed α-Alkylation of Nitriles with Primary Alcohols

被引:107
|
作者
Jana, Akash [1 ]
Reddy, C. Bal [1 ]
Maji, Biplab [1 ]
机构
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, India
来源
ACS CATALYSIS | 2018年 / 8卷 / 10期
关键词
homogeneous catalysis; bifunctional ligand; borrowing hydrogen; alcohols; manganese; PINCER COMPLEXES; BORROWING HYDROGEN; N-ALKYLATION; DEHYDROGENATION REACTIONS; SECONDARY ALCOHOLS; BOND FORMATION; C-ALKYLATION; AMINES; KETONES; ARYLACETONITRILES;
D O I
10.1021/acscatal.8b02998
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
The manganese(I) complex bearing a bidentate hydrazone ligand efficiently catalyzes the alpha-alkylations of nitrile using primary alcohols as alkylating agents. alpha-Functionalized nitriles were selectively obtained in good to excellent yields. The reaction is environmentally benign, producing water as the sole byproduct. Both benzylic and aliphatic alcohols could be used and functional groups were tolerated.
引用
收藏
页码:9226 / 9231
页数:11
相关论文
共 50 条
  • [1] Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols
    Chakraborty, Subrata
    Das, Uttam Kumar
    Ben-David, Yehoshoa
    Milstein, David
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (34) : 11710 - 11713
  • [2] Chemoselective α-Alkylation of Nitriles with Primary Alcohols by Manganese(I)-Catalysis
    Bera, Krishanu
    Mukherjee, Arup
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (13)
  • [3] Nickel-catalyzed alkylation of ketones and nitriles with primary alcohols
    Genc, Sertac
    Arslan, Burcu
    Gulcemal, Derya
    Gulcemal, Suleyman
    Gunnaz, Salih
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (48) : 9753 - 9762
  • [4] Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols
    Paudel, Keshav
    Xu, Shi
    Ding, Keying
    ORGANIC LETTERS, 2021, 23 (13) : 5028 - 5032
  • [5] Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis
    Borghs, Jannik C.
    Mai Anh Tran
    Sklyaruk, Jan
    Rueping, Magnus
    El-Sepelgy, Osama
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7927 - 7935
  • [6] Iron-Catalyzed Alkylation of Nitriles with Alcohols
    Ma, Wei
    Cui, Suiya
    Sun, Huamin
    Tang, Weijun
    Xue, Dong
    Li, Chaoqun
    Fan, Juan
    Xiao, Jianliang
    Wang, Chao
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (50) : 13118 - 13123
  • [7] Cobalt-Catalyzed Alkylation of Nitriles with Alcohols
    Singh, Arpita
    Findlater, Michael
    ORGANOMETALLICS, 2021, 41 (22) : 3145 - 3151
  • [8] First Intramolecular Alkylation of Nitriles with Primary and Secondary Alcohols Catalyzed by Iridium Complexes
    Anxionnat, Bruno
    Pardo, Domingo Gomez
    Ricci, Gino
    Cossy, Janine
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) : 4453 - 4456
  • [9] Manganese-Catalyzed α-Olefination of Nitriles with Secondary Alcohols
    Yadav, Vinita
    Landge, Vinod G.
    Subaramanian, Murugan
    Balaraman, Ekambaram
    ACS CATALYSIS, 2020, 10 (02): : 947 - 954
  • [10] Manganese-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols under Phosphine-Free Conditions
    Liu, Tingting
    Wang, Liandi
    Wu, Kaikai
    Yu, Zhengkun
    ACS CATALYSIS, 2018, 8 (08): : 7201 - 7207