Solvent-free synthesis of aryl ethers promoted by tetrabutylammonium fluoride

被引：2

作者：

Xiong, Wei ^{[1
]}

Ding, Quansheng ^{[1
]}

Chen, Jiuxi ^{[1
]}

Ding, Jinchang ^{[1
,2
]}

Wu, Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2010年 / 07期

关键词：

tetrabutylammonium fluoride; aryl ethers; solvent-free conditions; DIARYL ETHERS; EFFICIENT; CATALYST; PYRROLES; SC(OTF)(3); COMPLEXES; ALDEHYDES; STRATEGY; PHENOLS; ACID;

D O I：

10.3184/030823410X12791804205820

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of aryl fluorides with silyl reagents has been shown to be efficiently promoted by tetrabutylammonium fluoride, providing aryl ethers with good to excellent yields under solvent-free conditions. The efficiency of this reaction was demonstrated by the compatibility with aldehyde, nitro, cyano and acetyl groups. Moreover, the rigorous exclusion of air/moisture was not required in these transformations which proceeded under milder conditions than previously reported reactions of this type.

引用

页码：395 / 398

页数：4

共 34 条

[1] PALLADIUM-CATALYZED FORMYLATION OF ORGANIC HALIDES WITH CARBON-MONOXIDE AND TIN HYDRIDE [J].

BAILLARGEON, VP ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :452-461

[2] Rapid and efficient solid phase syntheses of cyclic peptides with endocyclic biaryl ether bonds [J].

Burgess, K ;

Lim, D ;

BoisChoussy, M ;

Zhu, JP .

TETRAHEDRON LETTERS, 1997, 38 (19) :3345-3348

[3] Indium(III)-catalyzed synthesis of N-substituted pyrroles under solvent-free conditions [J].

Chen, Jiu-Xi ;

Liu, Miao-Chang ;

Yang, Xiao-Liang ;

Ding, Jin-Chang ;

Wu, Hua-Yue .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (05) :877-883

[4] An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions [J].

Chen, Jiuxi ;

Wu, Huayue ;

Zheng, Zhiguo ;

Jin, Can ;

Zhang, Xingxian ;

Su, Weike .

TETRAHEDRON LETTERS, 2006, 47 (30) :5383-5387

[5] Approach to Synthesis of -Enamino Ketones and Pyrroles Catalyzed by Gallium(III) Triflate Under Solvent-Free Conditions [J].

Chen, Jiuxi ;

Yang, Xiaoliang ;

Liu, Miaochang ;

Wu, Huayue ;

Ding, Jinchang ;

Su, Weike .

SYNTHETIC COMMUNICATIONS, 2009, 39 (23) :4180-4198

[6] Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction [J].

Chen, Xi'an ;

Zhang, Changfu ;

Wu, Huayue ;

Yu, Xiaochun ;

Su, Weike ;

Cheng, Jiang .

SYNTHESIS-STUTTGART, 2007, (20) :3233-3239

[7] Total synthesis of anti-HIV agent chloropeptin I [J].

Deng, HB ;

Jung, JK ;

Liu, T ;

Kuntz, KW ;

Snapper, ML ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9032-9034

[8] Synthesis of the orienticin C M(2-4) macrocycle utilizing a nucleophilic aromatic substitution strategy [J].

Evans, DA ;

Watson, PS .

TETRAHEDRON LETTERS, 1996, 37 (19) :3251-3254

[9]

Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2700, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO

[10]

2-P

← 1 2 3 4 →