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 84 条
[31]   Efficient FeIII-catalyzed synthesis of bis(indolyl)methanes in ionic liquids [J].
Ji, SJ ;
Zhou, MF ;
Gu, DG ;
Jiang, ZQ ;
Loh, TP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1584-1587
[32]   LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature [J].
Ji, Xinfei ;
Huang, Tao ;
Wu, Wei ;
Liang, Fang ;
Cao, Song .
ORGANIC LETTERS, 2015, 17 (20) :5096-5099
[33]   N-Heterocyclic carbene-catalyzed aza-Michael addition [J].
Kang, Qiang ;
Zhang, Yugen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) :6715-6720
[34]   Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes [J].
Kano, T ;
Sasaki, K ;
Maruoka, K .
ORGANIC LETTERS, 2005, 7 (07) :1347-1349
[35]   An efficacious "naked-eye" selective sensing of cyanide from aqueous solutions using a triarylmethane leuconitrile [J].
Kaur, Paramjit ;
Sareen, Divya ;
Kaur, Sandeep ;
Singh, Amaljit .
INORGANIC CHEMISTRY COMMUNICATIONS, 2009, 12 (03) :272-275
[36]   Basicity of a stable carbene, 1,3-di-tert-butylimidazol-2-ylidene, in THF [J].
Kim, YJ ;
Streitwieser, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5757-5761
[37]   Chiral Bronsted acid catalyzed intermolecular Friedel-Crafts alkylation of styrenes with indoles: construction of all-carbon quaternary stereocenters [J].
Li, Ming-Li ;
Chen, Dian-Feng ;
Luo, Shi-Wei ;
Wu, Xiang .
TETRAHEDRON-ASYMMETRY, 2015, 26 (04) :219-224
[38]   Catalytic selective bis-arylation of imines with anisole, phenol, thioanisole and analogues [J].
Liu, Cong-Rong ;
Li, Man-Bo ;
Yang, Cui-Feng ;
Tian, Shi-Kai .
CHEMICAL COMMUNICATIONS, 2008, (10) :1249-1251
[39]   Copper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes [J].
Lopez, Aurora ;
Parra, Alejandro ;
Jarava-Barrera, Carlos ;
Tortosa, Mariola .
CHEMICAL COMMUNICATIONS, 2015, 51 (100) :17684-17687
[40]   Copper-Catalyzed Enantioselective 1,6-Boration of para-Quinone Methides and Efficient Transformation of gem-Diarylmethine Boronates to Triarylmethanes [J].
Lou, Yazhou ;
Cao, Peng ;
Jia, Tao ;
Zhang, Yongling ;
Wang, Min ;
Liao, Jian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) :12134-12138