Bismuth trichloride catalyzed efficient reductive etherification of carbonyl compounds with alcohols: A novel method for preparation of symmetrical and unsymmetrical ethers

被引：35

作者：

Wada, M ^{[1
]}

Nagayama, S ^{[1
]}

Mizutani, K ^{[1
]}

Hiroi, R ^{[1
]}

Miyoshi, N ^{[1
]}

机构：

[1] Univ Tokushima, Fac Integrated Arts & Sci, Dept Chem, Tokushima 7708502, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 02期

关键词：

D O I：

10.1246/cl.2002.248

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reductive homocoupling of a carbonyl compound and heterocoupling of a carbonyl compound with a non-protected alcohol were both effected smoothly at room temperature with triethylsilane in the presence of a catalytic amount of bismuth trichloride to afford the corresponding ethers in good yields.

引用

页码：248 / 249

页数：2

共 7 条

[1] SILANE REDUCTIONS IN ACIDIC MEDIA .1. REDUCTION OF ALDEHYDES AND KETONES IN ALCOHOLIC ACIDIC MEDIA - GENERAL SYNTHESIS OF ETHERS [J].

DOYLE, MP ;

DEBRUYN, DJ ;

KOOISTRA, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (10) :3659-&

[2] 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

[3] 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

[4] 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

[5] Bismuth bromide as an efficient and versatile catalyst for the cyanation and allylation of carbonyl compounds and acetals with organosilicon reagents [J].

Komatsu, N ;

Uda, M ;

Suzuki, H ;

Takahashi, T ;

Domae, T ;

Wada, M .

TETRAHEDRON LETTERS, 1997, 38 (41) :7215-7218

[6] SYNTHETIC STUDIES ON THE DIOXEPANE REGION OF BREVETOXIN-B - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF OXEPANES AND SYNTHESIS OF A MODEL FOR THE CDEF RING SKELETON OF BREVETOXIN-B [J].

NICOLAOU, KC ;

HWANG, CK ;

NUGIEL, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4136-4137

[7]

Suzuki T, 1999, SYNTHESIS-STUTTGART, P1561

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