A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride

被引：46

作者：

Iwanami, K ^{[1
]}

Seo, H ^{[1
]}

Tobita, Y ^{[1
]}

Oriyama, T ^{[1
]}

机构：

[1] Ibaraki Univ, Fac Sci, Dept Environm Sci, Mito, Ibaraki 3108512, Japan

来源：

SYNTHESIS-STUTTGART | 2005年 / 02期

关键词：

reductive etherification; iron(III) chloride; alkoxytrimethylsilane; triethylsilane; carbonyl compounds;

D O I：

10.1055/s-2004-834942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile reductive etherification of carbonyl compounds can be conveniently performed by reaction with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained in good to excellent yields under mild reaction conditions.

引用

页码：183 / 186

页数：4

共 18 条

[1] ALCL3-N,N-DIMETHYLANILINE - A NOVEL BENZYL AND ALLYL ETHER CLEAVAGE REAGENT [J].

AKIYAMA, T ;

HIROFUJI, H ;

OZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (07) :1932-1938

[2] REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE - NUCLEAR VERSUS BENZYLIC NUCLEOPHILIC-SUBSTITUTION [J].

ALONSO, F ;

BARBA, I ;

YUS, M .

TETRAHEDRON, 1990, 46 (06) :2069-2080

[3] 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

[4] Three-electron S(N)2 reactions of arylcyclopropane cation radicals .2. Steric and electronic effects of substitution [J].

Dinnocenzo, JP ;

Zuilhof, H ;

Lieberman, DR ;

Simpson, TR ;

McKechney, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :994-1004

[5]

Green T.W., 1999, PROTECTIVE GROUPS OR, p[76, 708]

[6]

HARTZ N, 1992, SYNLETT, P569

[7] EFFICIENT REDUCTIVE ETHERIFICATION OF CARBONYL-COMPOUNDS WITH ALKOXYTRIMETHYLSILANES [J].

HATAKEYAMA, S ;

MORI, H ;

KITANO, K ;

YAMADA, H ;

NISHIZAWA, M .

TETRAHEDRON LETTERS, 1994, 35 (25) :4367-4370

[8] A NOVEL METHOD FOR THE PREPARATION OF SYMMETRICAL AND UNSYMMETRICAL ETHERS - TRITYL PERCHLORATE PROMOTED REDUCTION OF CARBONYL-COMPOUNDS WITH TRIETHYLSILANE [J].

KATO, J ;

IWASAWA, N ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1985, (06) :743-746

[9] Bismuth bromide-catalyzed reductive coupling of carbonyl compounds and its application to the synthesis of novel crownophanes [J].

Komatsu, N ;

Ishida, J ;

Suzuki, H .

TETRAHEDRON LETTERS, 1997, 38 (41) :7219-7222

[10] Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers [J].

Kopecky, DJ ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :191-198

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