Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Arenes and Arylboronic Acids through C(sp2)-H Thianthrenation

被引:24
作者
Zhang, Jiajun [1 ,2 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Liaoning, Peoples R China
[2] Leibniz Inst Katalyse EV, D-18059 Rostock, Germany
关键词
CONVENIENT METHOD; BENZOPHENONE; AGENTS;
D O I
10.1021/acs.orglett.3c00792
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of mild methodology for converting inert C-H bonds to value-added molecules has been an attractive research topic during the last few decades as it offers efficient preparation. Meanwhile, diaryl ketones hold potent applications in antitumor drugs, the agrochemical industry, and synthetic chemistry. Herein, we report versatile palladium-catalyzed carbonylative cross-coupling reactions of aryl thianthrenium salts with arylboronic acids. Arenes were transformed site selectively via C(sp2)-H thianthrenation, and various desired diaryl ketones were produced in good to excellent yields.
引用
收藏
页码:2162 / 2166
页数:5
相关论文
共 35 条
  • [1] Late-Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α-Amino Alkyl Radicals
    Alvarez, Eva Maria
    Karl, Teresa
    Berger, Florian
    Torkowski, Luca
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (24) : 13609 - 13613
  • [2] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation
    Aukland, Miles H.
    Siauciulis, Mindaugas
    West, Adam
    Perry, Gregory J. P.
    Procter, David J.
    [J]. NATURE CATALYSIS, 2020, 3 (02) : 163 - 169
  • [3] Beller, 2013, CARBONYLATIVE CROSS
  • [4] Site-selective and versatile aromatic C-H functionalization by thianthrenation
    Berger, Florian
    Plutschack, Matthew B.
    Riegger, Julian
    Yu, Wanwan
    Speicher, Samira
    Ho, Matthew
    Frank, Nils
    Ritter, Tobias
    [J]. NATURE, 2019, 567 (7747) : 223 - 228
  • [5] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds
    Brennfuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4114 - 4133
  • [6] Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 2003-2004
    Calafat, Antonia M.
    Wong, Lee-Yang
    Ye, Xiaoyun
    Reidy, John A.
    Needham, Larry L.
    [J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 2008, 116 (07) : 893 - 897
  • [7] Albendazole and Mebendazole as Anti-Parasitic and Anti-Cancer Agents: an Update
    Chai, Jong-Yil
    Jung, Bong-Kwang
    Hong, Sung-Jong
    [J]. KOREAN JOURNAL OF PARASITOLOGY, 2021, 59 (03) : 189 - 225
  • [8] Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
    Chen, Junting
    Li, Jiakun
    Plutschack, Matthew B.
    Berger, Florian
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5616 - 5620
  • [9] Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes
    Chen, Xiao-Yue
    Wu, Yichen
    Wang, Peng
    [J]. SYNTHESIS-STUTTGART, 2022, 54 (18): : 3928 - 3940
  • [10] para-Selective arylation and alkenylation of monosubstituted arenes using thianthrene S-oxide as a transient mediator
    Chen, Xiao-Yue
    Nie, Xiao-Xue
    Wu, Yichen
    Wang, Peng
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (37) : 5058 - 5061