Expedient access to unsymmetrical triarylmethanes through N-heterocyclic carbene catalysed 1,6-conjugate addition of 2-naphthols to para-quinone methides

被引:61
|
作者
Arde, Panjab [1 ]
Anand, Ramasamy Vijaya [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Sect 81, Manauli Po 140306, Punjab, India
关键词
FRIEDEL-CRAFTS REACTIONS; CARBON ACID PK(A); AROMATIC-ALDEHYDES; SEQUENTIAL ARYLATION; ASYMMETRIC-SYNTHESIS; CROSS-COUPLINGS; BENZYL HALIDES; ESTERS; ARENES; DIARYLMETHANES;
D O I
10.1039/c6ra11116e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The utility of N-heterocyclic carbene as a Bronsted base catalyst for the synthesis of functionalised unsymmetrical triarylmethanes from 2-naphthol and para-quinone methides is described. This protocol allows the installation of naphthyl substituents on p-quinone methides through 1,6-conjugate addition to deliver the unsymmetrical triarylmethanes in good to excellent yields. Mild reaction conditions and 100% atom economy make this method synthetically advantageous over the other hitherto known methods.
引用
收藏
页码:77111 / 77115
页数:5
相关论文
共 50 条
  • [31] Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters
    Wang, Yi-Feng
    Wang, Chao-Jie
    Feng, Qing-Zhou
    Zhai, Jing-Jing
    Qi, Suo-Suo
    Zhong, Ai-Guo
    Chu, Ming-Ming
    Xu, Dan-Qian
    CHEMICAL COMMUNICATIONS, 2022, 58 (46) : 6653 - 6656
  • [32] Base-mediated 1,6-conjugate addition of the Seyferth-Gilbert reagent to para-quinone methides
    Gupta, Ashis Kumar
    Ahamad, Shakir
    Vaishanv, Narendra Kumar
    Kant, Ruchir
    Mohanan, Kishor
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (25) : 4623 - 4627
  • [33] Asymmetric 1,6-Conjugate Addition of para-Quinone Methides for the Synthesis of Chiral β,β-Diaryl-α-Hydroxy Ketones
    Gao, Yuan-Yuan
    Hua, Yuan-Zhao
    Wang, Min-Can
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 80 - 85
  • [34] Hf(OTf)4-Catalyzed 1,6-Conjugate Addition of 2-Alkyl-azaarenes to para-Quinone Methides
    Liu, Xinyuan
    Liu, Binbin
    Shi, Zhan
    Tan, Chen
    Fan, Rong
    Li, Zhi
    Tan, Jiajing
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3615 - 3624
  • [35] Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters
    Wang, Zhaobin
    Wong, Yuk Fai
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13711 - 13714
  • [36] Asymmetric Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides Using [1,2]-Phospha-Brook Rearrangement
    Tan, Qingfa
    Guo, Ning
    Yang, Linhan
    Wang, Fei
    Feng, Xiaoming
    Liu, Xiaohua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9332 - 9342
  • [37] Enantioselective Rauhut-Currier-Type 1,6-Conjugate Addition of Methyl Vinyl Ketone to para-Quinone Methides
    Kang, Tian-Chen
    Wu, Lu-Ping
    Yu, Qi-Wen
    Wu, Xin-Yan
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (27) : 6509 - 6513
  • [38] Metal-Free Regioselective 1,6-Conjugate Addition of Sulfide to para-Quinone Methides: Simple Access to E-Selective Thiaoxacyclophanes
    Kotha, Sambasivarao
    Gupta, Naveen K.
    Solanke, Balaji U.
    CHEMISTRYSELECT, 2023, 8 (34):
  • [39] TBAB-catalyzed 1,6-conjugate diazotization of para-quinone methides: A very effective access to polysubstituted α-diazocarbonyl compounds
    Liu, Zhang-Qin
    Liu, Sheng-Shu
    Guan, Xiao-Yu
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2024, 28 (03)
  • [40] Catalyst-free 1,6-conjugate addition of indoles and 4-hydroxycoumarins topara-quinone methides: synthesis of unsymmetrical triarylmethanes
    Kumaran, Subramani
    Prabhakaran, Mohan
    Mariyammal, Narayanan
    Parthasarathy, Kanniyappan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (39) : 7837 - 7841