Bronsted acid-catalyzed benzylation of 1,3-dicarbonyl derivatives

被引：116

作者：

Sanz, Roberto

Miguel, Delia

Martinez, Alberto

Alvarez-Gutierrez, Julia M.

Rodriguez, Felix

机构：

[1] Univ Burgos, Dept Quim, Area Quim Organ, Fac Ciencias, Burgos 09001, Spain

[2] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 10期

关键词：

D O I：

10.1021/ol070624a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Bronsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are carried out in air using undried solvents, with water being the only side product of the process.

引用

收藏

页码：2027 / 2030

页数：4

相关论文

共 25 条

[1] HYDRIDE TRANSFER MECHANISMS IN STRONGLY ACID MEDIA - THE REDUCTION OF CARBONIUM IONS BY ALCOHOLS AND AN EVALUATION OF THE BASIC STRENGTH OF ISOPROPYL ALCOHOL [J].

BARTLETT, PD ;

MCCOLLUM, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (07) :1441-1450

[2]

Bisaro F, 2002, SYNLETT, P1823

[3] Palladium-catalyzed intramolecular hydroalkylation of alkenyl-β-keto esters, α-aryl ketones, and alkyl ketones in the presence of Me3SiCl or HCl [J].

Han, XQ ;

Wang, X ;

Pei, T ;

Widenhoefer, RA .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (24) :6333-6342

[4] 2,3,6,7,10,11-hexamethoxytribenzotriquinacene: Synthesis, solid-state structure, and functionalization of a rigid analogue of cyclotriveratrylene [J].

Harig, M ;

Neumann, B ;

Stammler, HG ;

Kuck, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (11) :2381-2397

[5] Investigation of the behavior of arenediazonium salts with olefins in BmimPF6 [J].

Kabalka, GW ;

Dong, G ;

Venkataiah, B .

TETRAHEDRON LETTERS, 2004, 45 (13) :2775-2777

[6] Efficient Bronsted acid catalyzed Hosomi-Sakurai reaction of acetals [J].

Kampen, Daniela ;

List, Benjamin .

SYNLETT, 2006, (16) :2589-2592

[7] Perchloric acid adsorbed on silica gel (HClO4-SiO2) as an inexpensive, extremely efficient, and reusable dual catalyst system for acetal/ketal formation and their deprotection to aldehydes/ketones [J].

Kumar, Raj ;

Kumar, Dinesh ;

Chakraborti, Asit K. .

SYNTHESIS-STUTTGART, 2007, (02) :299-303

[8] Disproportionation reaction of diarylmethylisopropyl ethers: a versatile access to diarylmethanes from diarylcarbinols speeded up by the use of microwave irradiation [J].

L'Hermite, Nathalie ;

Giraud, Anne ;

Provot, Olivier ;

Peyrat, Jean-Francois ;

Alami, Mouad ;

Brion, Jean-Daniel .

TETRAHEDRON, 2006, 62 (51) :11994-12002

[9] Bronsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins [J].

Li, Zigang ;

Zhang, Junliang ;

Brouwer, Chad ;

Yang, Cai-Guang ;

Reich, Nicholas W. ;

He, Chuan .

ORGANIC LETTERS, 2006, 8 (19) :4175-4178

[10] BF3.OEt2-mediated C-C bond-forming reaction of α-hydroxyketene-(S,S)-acetals with active methylene compounds and its application in the synthesis of substituted 3,4-dihydro-2-pyridones [J].

Liu, Jun ;

Liang, Fushun ;

Liu, Qun ;

Li, Bing .

SYNLETT, 2007, (01) :156-160