Reductive coupling of carbonyl compounds to pinacols with zinc in THF-saturated aqueous ammonium chloride

被引：23

作者：

Hekmatshoar, R ^{[1
]}

Yavari, I

Beheshtiha, YS

Heravi, MM

机构：

[1] Azzahra Univ, Sch Sci, Dept Chem, Tehran, Iran

[2] Univ Tarbiat Modarres, Dept Chem, Tehran, Iran

来源：

MONATSHEFTE FUR CHEMIE | 2001年 / 132卷 / 06期

关键词：

carbonyl compounds; pinacols; zinc; pinacolization; carbon-carbon bond formation;

D O I：

10.1007/s007060170083

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of metallic zinc, aldehydes and ketones experience reductive coupling in tetrahydrofuran-saturated aqueous ammonium chloride (5:3) to afford the corresponding pinacols in moderate to high yields.

引用

页码：689 / 691

页数：3

共 11 条

[1] REACTIONS OF CP2TI(CO)2 WITH ALDEHYDES AND KETONES [J].

CHEN, TL ;

CHAN, TH ;

SHAVER, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 268 (01) :C1-C6

[2] A NOVEL REACTION TYPE PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE - SYNTHESIS OF ALLYLIC PINACOLS [J].

CLERICI, A ;

PORTA, O .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (10) :1690-1694

[3] NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].

COREY, EJ ;

DANHEISER, RL ;

CHANDRASEKARAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265

[4]

EINHORN C, 1989, SYNTHESIS-STUTTGART, P787

[5] MAGNESIUM-INDUCED AND TITANIUM-INDUCED REDUCTIVE COUPLING OF CARBONYL-COMPOUNDS - EFFICIENT SYNTHESES OF PINACOLS AND ALKENES [J].

FURSTNER, A ;

CSUK, R ;

ROHRER, C ;

WEIDMANN, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1729-1734

[6] GENERATION OF METAL-FREE SILYL ANIONS FROM DISILANES AND FLUORIDE CATALYST - SYNTHETIC REACTIONS WITH ALDEHYDES AND 1,3-DIENES [J].

HIYAMA, T ;

OBAYASHI, M ;

MORI, I ;

NOZAKI, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :912-914

[7]

IMAI T, 1993, SYNTHESIS-STUTTGART, P395

[8] BIMOLECULAR REDUCTIONS OF AROMATIC KETONES AND ALDEHYDES WITH THE NORMAL-BUTYLLITHIUM-FE4S4(SPH)4 SYSTEM [J].

INOUE, H ;

SUZUKI, M ;

FUJIMOTO, N .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1722-1724

[9] REDUCTIVE COUPLING OF AROMATIC-ALDEHYDES BY OCTACARBONYL DIFERRATE [J].

ITO, K ;

NAKANISHI, S ;

OTSUJI, Y .

CHEMISTRY LETTERS, 1980, (09) :1141-1144

[10]

LUBINEAU A, 1994, SYNTHESIS-STUTTGART, P741

← 1 2 →