Lanthanide(III) triflate-catalyzed thermal- and microwave-assisted synthesis of benzyl ethers from benzyl alcohols

被引:10
作者
Handlon, AL [1 ]
Guo, Y [1 ]
机构
[1] GlaxoSmithKline, Dept Med Chem, Res Triangle Pk, NC 27709 USA
关键词
condensation; ethers; lanthanides; Lewis acids; microwave;
D O I
10.1055/s-2004-836063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The lanthanide(III) trifluoromethanesulfonate-catalyzed condensation of benzyl alcohols with primary and secondary alcohols is described. This reaction proceeds readily with benzyl alcohols that have an alkyl or aryl substituent at the alpha-, ortho-, or para-position using microwave radiation or heating. The intramolecular variant of this reaction leads to cyclic benzofurans.
引用
收藏
页码:111 / 114
页数:4
相关论文
共 9 条
[1]   SmI2/water/amine mediates cleavage of allyl ether protected alcohols:: Application in carbohydrate synthesis and mechanistic considerations [J].
Dahlén, A ;
Sundgren, A ;
Lahmann, M ;
Oscarson, S ;
Hilmersson, G .
ORGANIC LETTERS, 2003, 5 (22) :4085-4088
[2]   Rare earth metal trifluoromethanesulfonates catalyzed benzyl-etherification [J].
Kawada, A ;
Yasuda, K ;
Abe, H ;
Harayama, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (03) :380-383
[3]   Rare-earth metal triflates in organic synthesis [J].
Kobayashi, S ;
Sugiura, M ;
Kitagawa, H ;
Lam, WWL .
CHEMICAL REVIEWS, 2002, 102 (06) :2227-2302
[4]   Secondary benzylation using benzyl alcohols catalyzed by lanthanoid, scandium, and hafnium triflate [J].
Noji, M ;
Ohno, T ;
Fuji, K ;
Futaba, N ;
Tajima, H ;
Ishii, K .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9340-9347
[5]   SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .81. SYNTHESIS OF AN OCTASACCHARIDE FRAGMENT OF HIGH-MANNOSE-TYPE GLYCANS OF GLYCOPROTEINS [J].
NUKADA, T ;
KITAJIMA, T ;
NAKAHARA, Y ;
OGAWA, T .
CARBOHYDRATE RESEARCH, 1992, 228 (01) :157-170
[6]   Yb(OTf)3/FeCl3 mediated facile conversion of alcohols, ketals and acid sensitive ethers into diphenylmethyl (DPM) ethers [J].
Sharma, GVM ;
Prasad, TR ;
Mahalingam, AK .
TETRAHEDRON LETTERS, 2001, 42 (04) :759-761
[7]  
Sharma GVM, 1999, J ORG CHEM, V64, P8943
[8]   Scandium (III) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols [J].
Tsuchimoto, T ;
Tobita, K ;
Hiyama, T ;
Fukuzawa, SI .
SYNLETT, 1996, (06) :557-&
[9]   Scandium(III) triflate-catalyzed Friedel-Crafts alkylation reactions [J].
Tsuchimoto, T ;
Tobita, K ;
Hiyama, T ;
Fukuzawa, S .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6997-7005