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

被引：59
|
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
来源：
RSC ADVANCES | 2016年 / 6卷 / 81期
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
  • [1] Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes
    Cheng, Yuyu
    Fang, Zhiqiang
    Jia, Yanwen
    Lu, Zhongyue
    Li, Wenjun
    Li, Pengfei
    RSC ADVANCES, 2019, 9 (42) : 24212 - 24217
  • [2] Recyclable Bismuth Complex Catalyzed 1,6-Conjugate Addition of Various Nucleophiles to para-Quinone Methides: Expedient Access to Unsymmetrical Diaryl- and Triarylmethanes
    Liang, Xianghao
    Xu, Haiyan
    Li, Hanlin
    Chen, Lizhuang
    Lu, Hongfei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (02) : 217 - 226
  • [3] 1,6-Conjugate Addition of 1,3-Dicarbonyl Compounds to para-Quinone Methides Enabled by Noncovalent N-Heterocyclic Carbene Catalysis
    Santra, Surojit
    Porey, Arka
    Guin, Joyram
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 477 - 486
  • [4] N-Heterocyclic Carbene Catalyzed 1,6-Conjugate Addition of Me3Si-CN to para-Quinone Methides and Fuchsones: Access to α-Arylated Nitriles
    Goswami, Prithwish
    Singh, Gurdeep
    Anand, Ramasamy Vijaya
    ORGANIC LETTERS, 2017, 19 (08) : 1982 - 1985
  • [5] Solvent-free 1,6-conjugate arylation of para-quinone methides: A greener approach to unsymmetrical triarylmethanes
    Hu, Yu
    Tang, Min
    Chen, Jia-Xuan
    Wei, Shi-Qian
    Tian, Yi
    Zhang, Liang-Dong
    Liu, Zhang-Qin
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2021, 25 (09)
  • [6] 1,6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones
    Guan, Xiao-Yu
    Zhang, Liang-Dong
    You, Peng-Sheng
    Liu, Sheng-Shu
    Liu, Zhang-Qin
    TETRAHEDRON LETTERS, 2019, 60 (03) : 244 - 247
  • [7] 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
  • [8] Organocatalyzed Asymmetric 1,6-Conjugate Addition of para-Quinone Methides with Dicyanoolefins
    Li, Xuanyi
    Xu, Xiuyan
    Wei, Weiwei
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2016, 18 (03) : 428 - 431
  • [9] Thiourea catalyzed 1,6-conjugate addition of indoles to para-quinone methides
    Wu, Guangmiao
    Li, Tao
    Liu, Fuhai
    Zhao, Yulong
    Ma, Shiqiang
    Tang, Shouchu
    Xie, Xingang
    She, Xuegong
    TETRAHEDRON LETTERS, 2021, 81
  • [10] Mn-Catalyzed 1,6-conjugate addition/aromatization of para-quinone methides
    Yang, Bobin
    Yao, Wei
    Xia, Xiao-Feng
    Wang, Dawei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (24) : 4547 - 4557
12345