Chemoselective α-Alkylation of Nitriles with Primary Alcohols by Manganese(I)-Catalysis

被引:5
|
作者
Bera, Krishanu [1 ]
Mukherjee, Arup [1 ]
机构
[1] Indian Inst Technol Bhilai, Dept Chem, GEC Campus, Raipur 492015, Chhattisgarh, India
关键词
Alkylation; Chemoselctive; Dehydrogenation; Manganese; Primary Alcohol; ONE-POT SYNTHESIS; C-C; CATALYZED ALKYLATION; ARYLACETONITRILES; MONOALKYLATION; ALKYLNITRILES; HYDROTALCITE; ACETONITRILE; COMPLEXES; STRATEGY;
D O I
10.1002/asia.202300157
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A sustainable and easy-to-use protocol for the alkylation of aryl nitriles with the earth-abundant manganese(I) catalyst is presented. The alkylation reaction employs readily available nitriles and naturally abundant alcohols as the coupling partners. The reaction proceeds chemoselectively and encompasses a broad substrate scope with good to excellent yields. The catalytic reaction yields selectively alpha-branched nitriles and water as the sole byproduct. Experimental studies were executed to understand the mechanism of the catalytic reaction.
引用
收藏
页数:8
相关论文
共 50 条
  • [21] Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles
    Ibrahim, Nada
    Hashmi, A. Stephen K.
    Rominger, Frank
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 461 - 468
  • [22] AN EFFICIENT AND CHEMOSELECTIVE SYNTHESIS OF NITRILES FROM PRIMARY AMIDES
    CLAREMON, DA
    PHILLIPS, BT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 59 - ORGN
  • [23] C-Alkylation of Secondary Alcohols by Primary Alcohols through Manganese-Catalyzed Double Hydrogen Autotransfer
    El-Sepelgy, Osama
    Matador, Esteban
    Brzozowska, Aleksandra
    Rueping, Magnus
    CHEMSUSCHEM, 2019, 12 (13) : 3099 - 3102
  • [24] AN EFFICIENT CHEMOSELECTIVE SYNTHESIS OF NITRILES FROM PRIMARY AMIDES
    CLAREMON, DA
    PHILLIPS, BT
    TETRAHEDRON LETTERS, 1988, 29 (18) : 2155 - 2158
  • [25] Manganese catalyzed C-alkylation of methyl N-heteroarenes with primary alcohols
    Jana, Akash
    Kumar, Amol
    Maji, Biplab
    CHEMICAL COMMUNICATIONS, 2021, 57 (24) : 3026 - 3029
  • [26] 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
  • [27] Manganese(I)-Catalyzed α-Alkenylation of Ketones Using Primary Alcohols
    Gawali, Suhas Shahaji
    Pandia, Biplab Keshari
    Gunanathan, Chidambaram
    ORGANIC LETTERS, 2019, 21 (10) : 3842 - 3847
  • [28] N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)
    Wei, Dongyue
    Yang, Peng
    Yu, Chuanman
    Zhao, Fengkai
    Wang, Yilei
    Peng, Zhihua
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2254 - 2263
  • [29] Synergistic Manganese(I) C-H Activation Catalysis in Continuous Flow: Chemoselective Hydroarylation
    Wang, Hui
    Pesciaioli, Fabio
    Oliveira, Joao C. A.
    Warratz, Svenja
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) : 15063 - 15067
  • [30] Manganese(I)-Catalyzed Cross-Coupling of Ketones and Secondary Alcohols with Primary Alcohols
    Gawali, Suhas Shahaji
    Pandia, Biplab Keshari
    Pal, Souvik
    Gunanathan, Chidambaram
    ACS OMEGA, 2019, 4 (06): : 10741 - 10754