Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

被引:15
作者
Brauer, Jan [1 ]
Quraishi, Elisabeth [1 ]
Kammer, Lisa Marie [1 ]
Opatz, Till [1 ]
机构
[1] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany
关键词
carboxylic acids; ketones; nickel; photocatalysis; radicals; N-C CLEAVAGE; AMIDES; ARYLATION; LIGAND; BONDS;
D O I
10.1002/chem.202103486
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1 degrees,2 degrees, benzylic, alpha-oxy & alpha-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.
引用
收藏
页码:18168 / 18174
页数:7
相关论文
共 53 条
  • [1] Recent advances in the synthesis of α-amino ketones
    Allen, Lewis A. T.
    Raclea, Robert-Cristian
    Natho, Philipp
    Parsons, Philip J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (03) : 498 - 513
  • [2] Direct Conversion of Carboxylic Acids to Alkyl Ketones
    Amani, Javad
    Molander, Gary A.
    [J]. ORGANIC LETTERS, 2017, 19 (13) : 3612 - 3615
  • [3] Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides
    Amani, Javad
    Alam, Rauful
    Badir, Shorouk
    Molander, Gary A.
    [J]. ORGANIC LETTERS, 2017, 19 (09) : 2426 - 2429
  • [4] Nickel: The "Spirited Horse" of Transition Metal Catalysis
    Ananikov, Valentine P.
    [J]. ACS CATALYSIS, 2015, 5 (03): : 1964 - 1971
  • [5] [Anonymous], 1969, ANGEW CHEM-GER EDIT, V81, P364
  • [6] [Anonymous], 2020, ANGEW CHEM-GER EDIT, V132, P17081
  • [7] [Anonymous], 2018, ANGEW CHEM, V130, P6720
  • [8] [Anonymous], 2015, ANGEW CHEM-GER EDIT, V127, P8040
  • [9] [Anonymous], 2019, ANGEW CHEM, V131, P1803
  • [10] [Anonymous], 2016, ANGEW CHEM, V128, P4108