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 42 条
  • [1] [Anonymous], 2013, ANGEW CHEM, V125, P14115
  • [2] [Anonymous], 2015, ANGEW CHEM, V127, P13366
  • [3] [Anonymous], 2014, ANGEW CHEM, V126, P76
  • [4] Monoalkylation of Acetonitrile by Primary Alcohols Catalyzed by Iridium Complexes
    Anxionnat, Bruno
    Pardo, Domingo Gomez
    Ricci, Gino
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2011, 13 (15) : 4084 - 4087
  • [5] Recent advances on non-precious metal-catalyzed C-H functionalization of N-heteroarenes
    Bera, Atanu
    Kabadwal, Lalit Mohan
    Bera, Sourajit
    Banerjee, Debasis
    [J]. CHEMICAL COMMUNICATIONS, 2021, 58 (01) : 10 - 28
  • [6] Nickel-catalyzed sustainable synthesis of N-heterocycles through dehydrogenative coupling of alcohols
    Bera, Krishanu
    Mukherjee, Arup
    [J]. TETRAHEDRON LETTERS, 2021, 81
  • [7] Nickel-catalyzed hydrogen-borrowing strategy: chemo-selective alkylation of nitriles with alcohols
    Bera, Sourajit
    Bera, Atanu
    Banerjee, Debasis
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (50) : 6850 - 6853
  • [8] Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis
    Borghs, Jannik C.
    Mai Anh Tran
    Sklyaruk, Jan
    Rueping, Magnus
    El-Sepelgy, Osama
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) : 7927 - 7935
  • [9] Osmium Catalyst for the Borrowing Hydrogen Methodology: α-Alkylation of Arylacetonitriles and Methyl Ketones
    Buil, Maria L.
    Esteruelas, Miguel A.
    Herrero, Juana
    Izquierdo, Susana
    Pastor, Isidro M.
    Yus, Miguel
    [J]. ACS CATALYSIS, 2013, 3 (09): : 2072 - 2075
  • [10] Dialkylamino cyclopentadienyl ruthenium(II) complex-catalyzed α-alkylation of arylacetonitriles with primary alcohols
    Cheung, Hung Wai
    Li, Juan
    Zheng, Wenxu
    Zhou, Zhongyuan
    Chiu, Yu Hin
    Lin, Zhenyang
    Lau, Chak Po
    [J]. DALTON TRANSACTIONS, 2010, 39 (01) : 265 - 274