Rare earth metal trifluoromethanesulfonates catalyzed benzyl-etherification

被引：32

作者：

Kawada, A

Yasuda, K

Abe, H

Harayama, T

机构：

[1] Nippon Steel Chem Co Ltd, Res & Dev Labs, Tobata Ku, Kitakyushu, Fukuoka 8048503, Japan

[2] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2002年 / 50卷 / 03期

关键词：

rare earth metal trifluoromethanesulfonate; benzyl-etherification; recyclable catalyst; benzyl alcohol; benzyl ether; Lewis acid;

D O I：

10.1248/cpb.50.380

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Rare earth metal trifluoromethanesulfonates [rare earth metal triflate, RE(OTf)(3)] were found to be efficient catalyst for benzyl-etherification. In the presence of a catalytic amount of RE(OTf)(3), condensation of benzyl alcohols and aliphatic alcohols proceeded smoothly to afford the benzyl ethers. The condensation between benzyl alcohols and thiols also proceeded, and thio ethers were obtained in good yield. In these reactions, RE(OTf)(3) could be recovered easily after the reactions were completed and could be reused without loss of activity.

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收藏

页码：380 / 383

页数：4

相关论文

共 29 条

[1] USE OF LANTHANIDE(III) IONS AS CATALYSTS FOR THE REACTIONS OF AMINES WITH NITRILES [J].

FORSBERG, JH ;

SPAZIANO, VT ;

BALASUBRAMANIAN, TM ;

LIU, GK ;

KINSLEY, SA ;

DUCKWORTH, CA ;

POTERUCA, JJ ;

BROWN, PS ;

MILLER, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1017-1021

[2] DIRECT SYNTHESIS OF THIOETHERS FROM THIOLS AND ALCOHOLS [J].

GUINDON, Y ;

FRENETTE, R ;

FORTIN, R ;

ROKACH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1357-1359

[3] AQUEOUS REACTIONS WITH A LEWIS-ACID AND AN ORGANOMETALLIC REAGENT - THE SCANDIUM TRIFLUOROMETHANESULFONATE-CATALYZED ALLYLATION REACTION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN [J].

HACHIYA, I ;

KOBAYASHI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6958-6960

[4] Ln(OTf)(3)-LiClO4 as reusable catalyst system for Friedel-Crafts acylation [J].

Kawada, A ;

Mitamura, S ;

Kobayashi, S .

CHEMICAL COMMUNICATIONS, 1996, (02) :183-184

[5] LANTHANIDE TRIFLUOROMETHANESULFONATES AS REUSABLE CATALYSTS - CATALYTIC FRIEDEL-CRAFTS ACYLATION [J].

KAWADA, A ;

MITAMURA, S ;

KOBAYASHI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) :1157-1158

[6]

KAWADA A, 1994, SYNLETT, P545

[7] Friedel-Crafts reactions catalyzed by rare earth metal trifluoromethanesulfonates [J].

Kawada, A ;

Mitamura, S ;

Matsuo, J ;

Tsuchiya, T ;

Kobayashi, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (10) :2325-2333

[8]

KAWADA A, 2000, Patent No. 2000204055

[9] DIRECT SYNTHESIS OF ETHERS VIA ZINC-CHLORIDE MEDIATED ETHERIFICATION OF ALCOHOLS IN DICHLOROETHANE [J].

KIM, SG ;

CHUNG, KN ;

YANG, SB .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3917-3919

[10] ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY CHIRAL LANTHANIDE(III) TRIFLUOROMETHANESULFONATES - UNIQUE STRUCTURE OF THE TRIFLATE AND STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS USING A SINGLE CHIRAL SOURCE AND A CHOICE OF ACHIRAL LIGANDS [J].

KOBAYASHI, S ;

ISHITANI, H ;

HACHIYA, I ;

ARAKI, M .

TETRAHEDRON, 1994, 50 (40) :11623-11636