Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

被引:18
|
作者
Zhao, Baoli [1 ,2 ]
Yin, Xiaoting [2 ]
Li, Haifeng [2 ]
Cheng, Kai [2 ]
Wan, Jie-Ping [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China
基金
中国国家自然科学基金;
关键词
VISIBLE-LIGHT-DRIVEN; ONE-POT SYNTHESIS; AEROBIC OXIDATION; BOND-CLEAVAGE; CHEMOSELECTIVE SYNTHESIS; DIARYL 1,2-DIKETONES; CATALYZED OXIDATION; BENZIL DERIVATIVES; CINNAMIC-ACIDS; EOSIN Y;
D O I
10.1039/d3qo00064h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free dioxygenative reaction of aryl diazonium salts with aryl alkynes for vicinal diketone synthesis is developed. Aerobic oxygenation and organic dye-based photocatalysis are the major advantages of the synthetic method. On the basis of rational control experiments, a photoredox mechanism involving free radical dioxygenation is proposed.
引用
收藏
页码:1942 / 1947
页数:6
相关论文
共 50 条
  • [1] SYNTHESIS OF NEW METAL-FREE DIAZONIUM SALTS AND THEIR APPLICATIONS TO MICROLITHOGRAPHY
    UCHINO, S
    HASHIMOTO, M
    IWAYANAGI, T
    POLYMERS IN MICROLITHOGRAPHY: MATERIALS AND PROCESSES, 1989, 412 : 319 - 331
  • [2] SYNTHESIS OF NEW METAL-FREE DIAZONIUM SALTS AND THEIR APPLICATIONS TO MICROLITHOGRAPHY
    UCHINO, S
    HASHIMOTO, M
    IWAYANAGI, T
    ACS SYMPOSIUM SERIES, 1989, 412 : 319 - 331
  • [3] SYNTHESIS OF NEW METAL-FREE DIAZONIUM SALTS AND THEIR APPLICATION TO MICROLITHOGRAPHY
    UCHINO, S
    HASHIMOTO, M
    IWAYANAGI, T
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 55 - PMSE
  • [4] Metal-Free S-Arylation of Cysteine Using Arenediazonium Salts
    Naveen, Naganaboina
    Sengupta, Saumitra
    Chandrasekaran, Srinivasan
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3562 - 3569
  • [5] Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts
    Kervefors, Gabriella
    Kersting, Leonard
    Olofsson, Berit
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (18) : 5790 - 5795
  • [6] Transition metal-free base-promoted arylation of sulfenate anions with diaryliodonium salts
    Wang, Lei
    Chen, Mingjie
    Zhang, Junliang
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (01): : 32 - 35
  • [7] Transition metal-free dimerization of alkynes using hypervalent iodine reagents
    Schoergenhumer, Johannes
    Waser, Mario
    TETRAHEDRON LETTERS, 2016, 57 (15) : 1678 - 1680
  • [8] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts
    Hari, Durga Prasad
    Schroll, Peter
    Koenig, Burkhard
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 2958 - 2961
  • [9] Metal-free stereoselective intramolecular oxyamination of alkynes using a robotic and rapid photocatalytic synthesis and screening system
    Lu, Jia-Min
    Mao, Yihui
    Guo, Qihang
    Zhong, Chengcheng
    Gao, Xian-Ge
    Fang, Qun
    Lu, Zhan
    GREEN CHEMISTRY, 2025, 27 (03) : 560 - 565
  • [10] TRANSITION METAL-FREE O-ARYLATION OF QUINOXALIN-2-ONES WITH DIARYLIODONIUM SALTS
    Kuriyama, Masami
    Mochizuki, Yuki
    Miyagi, Tsubasa
    Yamamoto, Kosuke
    Demizu, Yosuke
    Onomura, Osamu
    HETEROCYCLES, 2021, 103 (01) : 502 - 510