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

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

页码：77111 / 77115

页数：5

共 50 条

[41] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
Chu, Wen-Dao
Zhang, Le-Fen
Bao, Xu
Zhao, Xian-He
Zeng, Chao
Du, Ji-Yuan
Zhang, Guo-Biao
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
[42] 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
[43] Bismuth Triflate-Catalyzed Vinylogous Nucleophilic 1,6-Conjugate Addition of para-Quinone Methides with 3-Propenyl-2-silyloxyindoles
Xie, Kai-Xue
Zhang, Zhi-Pei
Li, Xin
ORGANIC LETTERS, 2017, 19 (24) : 6708 - 6711
[44] Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles
Deng, Yu-Hua
Zhang, Xiang-Zhi
Yu, Ke-Yin
Yan, Xu
Du, Ji-Yuan
Huang, Hanmin
Fan, Chun-An
CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4183 - 4186
[45] Bi(OTf)3 Catalyzed Solvent Free Approach to Unsymmetrical Diaryl(2-indolyl) methanes through 1,6-Conjugate Addition of 3-Substituted Indoles to para-Quinone Methides
Goswami, Prithwish
Anand, Ramasamy Vijaya
CHEMISTRYSELECT, 2016, 1 (10): : 2556 - 2559
[46] Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides
Chen, Min
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) : 4583 - 4587
[47] Synthesis of Quinone Methide Substituted Neonicotinoid Derivatives via 1,6-Conjugate Addition of N-Benzyl Nitro Ketene Aminals with para-Quinone Methides Accompanying Oxidation
Wang, Bao-Qu
Luo, Qin
Xiao, Qiang
Lin, Jun
Yan, Sheng-Jiao
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (09): : 8382 - 8389
[48] 1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives
Liu, Donglan
Xu, Haiyan
Hang, Yi
Lu, Hongfei
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 796 - 802
[49] TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water
Liu, Zhang-Qin
You, Peng-Sheng
Zhang, Liang-Dong
Liu, Da-Qing
Liu, Sheng-Shu
Guan, Xiao-Yu
MOLECULES, 2020, 25 (03):
[50] Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes
Cong Duan
Ling Ye
Wenqin Xu
Xinying Li
Feng Chen
Zhigang Zhao
Xuefeng Li
ChineseChemicalLetters, 2018, 29 (08) : 1273 - 1276

← 1 2 3 4 5 →