Photoinduced decarboxylative 1,6-addition of para-quinone methides with α-keto acids: an eco-friendly approach to α,α′-diarylated ketones

被引:6
|
作者
He, Chen [1 ]
Zhong, Yingfang [1 ]
Han, Huiqi [1 ]
Wang, Qi [1 ]
Xu, Lijing [1 ]
Zhang, Ting [1 ]
Hu, Yaqiong [1 ]
Huang, Qitong [1 ]
Liu, Jun [2 ]
Yang, Min [1 ]
机构
[1] Gannan Med Univ, Oil Tea Med Hlth Care & Funct Prod Dev Engn Res Ct, Sch Pharm, Key Lab Biomat & Biofabricat Tissue Engn Jiangxi P, Ganzhou 341000, Peoples R China
[2] Nanchang Univ, Affiliated Ganzhou Hosp, Dept Neurosurg, Ganzhou 341000, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
1,6-CONJUGATE ADDITION; EXPEDIENT ACCESS; P-QMS; ARYLATION; CYCLIZATION; ESTERS; ROUTE; BOND;
D O I
10.1039/d2nj04562a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photoinduced decarboxylative 1,6-addition of para-quinone methides with alpha-keto acids in an eco-friendly approach to alpha,alpha '-diarylated ketones is developed. This reaction proceeds smoothly with a broad substrate scope in the presence of cheap photocatalysts. Some of alpha,alpha '-diarylated ketones were applied as fluorescent dyes into the fluorescence spectrum and live-cell imaging.
引用
收藏
页码:21032 / 21036
页数:5
相关论文
共 50 条
  • [1] 1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
    Gao, Shang
    Xu, Xiuyan
    Yuan, Zhenbo
    Zhou, Haipin
    Yao, Hequan
    Lin, Aijun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 3006 - 3012
  • [2] Decarboxylative 1,6-Conjugate Addition of α-Keto Acids with Para-Quinone Methides Enabled by Photoredox Catalysis
    Wu Zijun
    Wang Jian
    ACTA CHIMICA SINICA, 2017, 75 (01) : 74 - 79
  • [3] Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to para-Quinone Methides
    Ali, Amjad
    Jajoria, Raveena
    Harit, Harish K.
    Singh, Ravi P.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (08): : 5213 - 5228
  • [4] Direct access to a,a′-diarylated ketones through N-heterocyclic carbene-catalyzed 1,6-addition of aromatic aldehydes to para-quinone methides
    Zhang, Guifu
    Jiang, Longxiang
    Shi, Wenjuan
    Zhou, Meiling
    Qiu, Fenghao
    Sun, Shaofa
    Wang, Jian
    Guo, Haibing
    SYNTHETIC COMMUNICATIONS, 2017, 47 (08) : 803 - 810
  • [5] Photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide and para-quinone methides via radical 1,6-addition
    Yang, Min
    Han, Huiqi
    Jiang, Hui
    Ye, Shengqing
    Fan, Xiaona
    Wu, Jie
    CHINESE CHEMICAL LETTERS, 2021, 32 (11) : 3535 - 3538
  • [6] Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6-Addition of Arylboronic Acids to Para-Quinone Methides
    Huang, Gong-Bin
    Huang, Wei-Hua
    Guo, Jing
    Xu, Dong-Liang
    Qu, Xiao-Chen
    Zhai, Pei-Hong
    Zheng, Xiu-Hua
    Weng, Jiang
    Lu, Gui
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1241 - 1246
  • [7] Photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide and para-quinone methides via radical 1,6-addition
    Min Yang
    Huiqi Han
    Hui Jiang
    Shengqing Ye
    Xiaona Fan
    Jie Wu
    ChineseChemicalLetters, 2021, 32 (11) : 3535 - 3538
  • [8] Acetic Acid-Catalyzed 1,6-Addition of Indolizine to para-Quinone Methides
    Lafzi, Ferruh
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (07)
  • [9] 1,6-Addition of indolizines to para-quinone methides with indium(III) chloride as catalyst
    Senna, Ana Julia S.
    Rodrigues Jr, Manoel T.
    Santos, Hugo
    Zeoly, Lucas A.
    Gomes, Ralph C.
    Coelho, Fernando
    TETRAHEDRON LETTERS, 2023, 125
  • [10] Alkoxylation of para-Quinone Methides via Bismuth Complex Catalyzed 1,6-Addition Reactions of Alcohols
    Li, Hanlin
    Liu, Donglan
    Chen, Liang
    Xu, Haiyan
    Lu, Hongfei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3279 - 3284