Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

被引:25
|
作者
Bains, Amreen K. [1 ]
Biswas, Ayanangshu [1 ]
Adhikari, Debashis [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Sas Nagar 140306, Punjab, India
关键词
nickel catalysis; cross-coupling; secondary alcohols; radical reaction; METHYLATION; QUINOLINE; METHANOL; CAMPHOR; AMIDES;
D O I
10.1002/adsc.202101077
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result alpha-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated alpha,beta-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction.
引用
收藏
页码:47 / 52
页数:6
相关论文
共 50 条
  • [21] Nickel-Catalyzed Monofluoroalkylation of Arylsilanes via Hiyama Cross-Coupling
    Wu, Yun
    Zhang, Hao-Ran
    Cao, Yi-Xuan
    Lan, Quan
    Wang, Xi-Sheng
    ORGANIC LETTERS, 2016, 18 (21) : 5564 - 5567
  • [22] Synthesis of Chiral α-Aryl Ketones by Photoredox/Nickel-Catalyzed Enantioconvergent Acyl Cross-Coupling with Organotrifluoroborate
    Wang, Weichen
    Shen, Chaoren
    Zhang, Linli
    Dong, Kaiwu
    ORGANIC LETTERS, 2024, 26 (04) : 850 - 854
  • [23] Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides
    Jensen, AE
    Knochel, P
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01): : 79 - 85
  • [24] Nickel-catalyzed sustainable synthesis of N-heterocycles through dehydrogenative coupling of alcohols
    Bera, Krishanu
    Mukherjee, Arup
    TETRAHEDRON LETTERS, 2021, 81
  • [25] Electrochemical nickel-catalyzed cross-coupling of glycosyl thiols with preactivated phenols and ketones
    Li, Fuxin
    Liu, Hui
    Xing, Wanyu
    Zhang, Qingju
    Wang, Liming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (18) : 3597 - 3601
  • [26] 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
  • [27] Nickel-catalyzed cross-coupling reactions of secondary alkyl halides.
    Fu, GC
    Zhou, JR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U30 - U30
  • [28] Regioselective Synthesis of Trialkylpyrazines via Nickel-Catalyzed Negishi Cross-Coupling of Pyrazine Triflate
    Pitchaiah, Arigala
    Hwang, In Taek
    Hwang, Jin-Soo
    Kim, Hyungrok
    Lee, Kee-In
    SYNTHESIS-STUTTGART, 2012, 44 (11): : 1631 - 1636
  • [29] Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
    Li, Zijian
    Sun, Wenxuan
    Wang, Xianxu
    Li, Luyang
    Zhang, Yong
    Li, Chao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (09) : 3536 - 3543
  • [30] Synthesis of Thioethers via Nickel-Catalyzed Cross-Coupling of Aryl Halides with Ketene Dithioacetal
    Xu, Baolong
    Ling, Shaowen
    Zheng, Shuaichen
    Feng, Xinyi
    Liu, Hui
    Dong, Yunhui
    Li, Xinjin
    Hong, Biqiong
    Sun, Feng-Gang
    ORGANIC LETTERS, 2025, 27 (07) : 1620 - 1625