B(C6F5)3: an efficient catalyst for reductive alkylation of alkoxy benzenes and for synthesis of triarylmethanes using aldehydes

被引：28

作者：

Chandrasekhar, S. ^{[1
]}

Khatun, Sanjida ^{[1
]}

Rajesh, G. ^{[1
]}

Reddy, Ch. Raji ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 48期

关键词：

Tris(pentafluorophenyl)borane; Polymethylhydrosiloxane; Reductive alkylation; Electron-rich arenes; Aldehyde; FRIEDEL-CRAFTS ALKYLATION; AROMATIC-ALDEHYDES; POLYMETHYLHYDROSILOXANE PMHS; PRACTICAL SYNTHESIS; GOLD(III) CHLORIDE; CARBONYL-COMPOUNDS; N-ALKYLATION; ARENES; DERIVATIVES; TRIHETEROARYLMETHANES;

D O I：

10.1016/j.tetlet.2009.09.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tris(pentafluorophenyl)borane [B(C6F5)(3)] has been used as an efficient catalyst for reductive alkylation of alkoxy benzenes using aldehydes as an alkylating agent in the presence of polymethylhydrosiloxane (PMHS). Various alkylated trimethoxybenzene derivatives have been prepared in good to high yields. In addition, B(C6F5)(3) was also used as a catalyst for the reaction of electron-rich arenes with aldehydes to obtain triarylmethanes. The use of reductive alkylation protocol for the synthesis of an isochroman and tetrallydroisoquinoline derivatives has also been demonstrated. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6693 / 6697

页数：5

共 45 条

[1] HYDRIDE SHIFTS IN FRIEDEL-CRAFTS REACTION OF ALLYL ALCOHOL WITH BENZENE [J].

ACKERMANN, W ;

HEESING, A .

CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (09) :3126-3133

[2] Novel and Highly Regioselective Friedel-Crafts Alkylation of 3,5-Dimethoxyaniline Using an Aldehyde and Triethylsilane as Reducing Agent [J].

Augustine, John Kallikat ;

Naik, Yanjerappa Arthoba ;

Mandal, Ashis Baran ;

Alagarsamy, Padma ;

Akabote, Vani .

SYNLETT, 2008, (16) :2429-2432

[3] A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. [J].

Babu, G ;

Sridhar, N ;

Perumal, PT .

SYNTHETIC COMMUNICATIONS, 2000, 30 (09) :1609-1614

[4] LEWIS ACID-INDUCED ELECTROPHILIC SUBSTITUTION OF INDOLE .3. [J].

BANERJI, J ;

CHATTERJEE, A ;

MANNA, S ;

PASCARD, C ;

PRANGE, T ;

SHOOLERY, JN .

HETEROCYCLES, 1981, 15 (01) :325-336

[5] Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors [J].

Bergh, Anders ;

Leffler, Hakon ;

Sundin, Anders ;

Nilsson, Ulf J. ;

Kann, Nina .

TETRAHEDRON, 2006, 62 (35) :8309-8317

[6] SYNTHESES AND REACTIONS OF ALLYLIC AND HOMOALLYLIC PYROPHOSPHATE TETRAESTERS [J].

BUTSUGAN, Y ;

NAGAI, K ;

NAGAYA, F ;

TABUCHI, H ;

YAMADA, K ;

ARAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (05) :1707-1714

[7] A facile and chemoselective conjugate reduction using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 [J].

Chandrasekhar, S ;

Chandrashekar, G ;

Reddy, MS ;

Srihari, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (09) :1650-1652

[8] Synthesis of trisubstituted alkenes by reductive dehydroxylation of Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 [J].

Chandrasekhar, S ;

Chandrashekar, G ;

Vijeender, K ;

Reddy, MS .

TETRAHEDRON LETTERS, 2006, 47 (20) :3475-3478

[9] Reductive etherification of carbonyl compounds with alkyl trimethylsilylethers using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 [J].

Chandrasekhar, S ;

Chandrashekar, G ;

Babu, BN ;

Vijeender, K ;

Reddy, KV .

TETRAHEDRON LETTERS, 2004, 45 (28) :5497-5499

[10] Rapid defunctionalization of carbonyl group to methylene with polymethylhydrosiloxane-B(C6F5)3 [J].

Chandrasekhar, S ;

Reddy, CR ;

Babu, BN .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9080-9082

← 1 2 3 4 5 →