Electrocatalytic Hydrogenation and Reductive Coupling of Aryl Ketones: Highly efficient Straightforward Metal-Free Access to Alcohols and Pinacols

被引:2
作者
Chowdhury, Sushobhan [1 ]
Kumar, Ajay [1 ]
机构
[1] CSIR, Med & Proc Chem Div, Cent Drug Res Inst, Lucknow 226031, Uttar Pradesh, India
关键词
aryl ketones; electrosynthesis; hydrogenation; modification of bioactive molecules; reductive pinacol coupling; ORGANOCATALYTIC TRANSFER HYDROGENATION; ASYMMETRIC TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; IONIC LIQUIDS; PHOTOREDUCTION; BENZOPHENONES; ACETOPHENONE; SELECTIVITY; CATALYSIS; DIAMINE;
D O I
10.1002/ajoc.202200425
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An electrocatalytic pathway is disclosed for the hydrogenation and reductive pinacol coupling of aryl ketones. The operationally simple protocol neither requires an external catalyst nor any sacrificial anode and proceeds efficiently under the aerobic condition at an ambient temperature and pressure. Under the optimized condition, diaryl ketones transform completely to the corresponding diarylmethanols whereas aryl ketones undergo reductive pinacol coupling leading to the respective 1,2-diol compounds in good to excellent yields. The protocol showed a high degree of substrate compatibility with moderate to very good diastereoselectivity depending on the substrates. The scope of the developed method was also extended to the different bioactive molecules opening up the possibility for their late-stage synthetic modification.
引用
收藏
页数:7
相关论文
共 60 条
  • [1] Abdel-Magid, 1998, ACS S SERIES
  • [2] Escobar EA, 2010, J MEX CHEM SOC, V54, P133
  • [3] [Anonymous], 2019, ANGEW CHEM, V131, P1773
  • [4] [Anonymous], 2008, ANGEW CHEM, V120, P3363
  • [5] Synthesis of 4-substituted ethers of benzophenone and their antileishmanial activities
    Arshia
    Ahad, Faiza
    Ghouri, Nida
    Kanwal
    Khan, Khalid Mohammed
    Perveen, Shahnaz
    Choudhary, M. Iqbal
    [J]. ROYAL SOCIETY OPEN SCIENCE, 2018, 5 (05):
  • [6] Hydrogen Transfer Reactions of Carbonyls, Alkynes, and Alkenes with Noble Metals in the Presence of Alcohols/Ethers and Amines as Hydrogen Donors
    Barath, Eszter
    [J]. CATALYSTS, 2018, 8 (12):
  • [7] Cyclopentadienyl-NHC Iron Complexes for Solvent-Free Catalytic Hydrosilylation of Aldehydes and Ketones
    Bezier, David
    Jiang, Fan
    Roisnel, Thierry
    Sortais, Jean-Baptiste
    Darcel, Christophe
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (09) : 1333 - 1337
  • [8] Brown HC, 1996, ACS SYM SER, V641, P1
  • [9] Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst
    Bruneau-Voisine, Antoine
    Wang, Ding
    Dorcet, Vincent
    Roisnel, Thierry
    Darcel, Christophe
    Sortais, Jean-Baptiste
    [J]. ORGANIC LETTERS, 2017, 19 (13) : 3656 - 3659
  • [10] Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: synthesis, characterization and catalytic transfer hydrogenation activity
    Byrne, Joseph P.
    Musembi, Pauline
    Albrecht, Martin
    [J]. DALTON TRANSACTIONS, 2019, 48 (31) : 11838 - 11847