Conversion of (sp3)C-F bonds of alkyl fluorides to (sp3)C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents

被引：19

作者：

Begum, Shameem Ara

Terao, Jun

Kambe, Nobuaki

机构：

[1] Osaka Univ, Sci & Technol Ctr Atoms Mol & Ions Control, Grad Sch Engn, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY LETTERS | 2007年 / 36卷 / 01期

关键词：

D O I：

10.1246/cl.2007.196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient method for conversion of (sp(3))C-F bonds to (sp(3))C-Z (Z = I, SR, SeR, TeR) bonds has been developed. The reaction proceeds at room temperature using magnesium salts (Z-MgX). S(N)2 mechanism for substitiution of primary alkyl fluorides with MgI2 in ether was supported by the inversion of the stereochemistry of the carbon connecting to F.

引用

收藏

页码：196 / 197

页数：2

相关论文

共 18 条

[1]

FILIPPO JS, 1975, J ORG CHEM, V40, P3295

[2] Low-valent niobium-mediated double activation of C-F/C-H bonds:: Fluorene synthesis from o-arylated α,α,α-trifluorotoluene derivatives [J].

Fuchibe, K ;

Akiyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1434-1435

[3] Alkylation of magnesium enamide with alkyl chlorides and fluorides [J].

Hatakeyama, T ;

Ito, S ;

Nakamura, M ;

Nakamura, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14192-14193

[4] On the dichotomy of the SN2/ET reaction pathways:: an apparent SN2 reactivity in the reaction of naphthalene dianion with alkyl fluorides [J].

Herrera, RP ;

Guijarro, A ;

Yus, M .

TETRAHEDRON LETTERS, 2003, 44 (06) :1309-1312

[5] Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane [J].

Hirano, K ;

Fujita, K ;

Yorimitsu, H ;

Shinokubo, H ;

Oshima, K .

TETRAHEDRON LETTERS, 2004, 45 (12) :2555-2557

[6]

Hiyama T., 2000, ORGANOFLUORINE COMPO

[7]

KIRRMANN A, 1969, CR ACAD SCI C CHIM, V268, P547

[8] THE ROLE OF LIALH4 IN THE PHOTOLYSIS OF BENZYL FLUORIDE DERIVATIVES [J].

KOSMRLJ, B ;

KRALJ, B ;

SKET, B .

TETRAHEDRON LETTERS, 1995, 36 (43) :7921-7924

[9] Aliphatic and aromatic carbon-fluorine bond activation with CP*2ZrH2:: Mechanisms of hydrodefluorination [J].

Kraft, BM ;

Lachicotte, RJ ;

Jones, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10973-10979

[10] HALOGEN-EXCHANGE REACTIONS BETWEEN ALKYL FLUORIDES AND BORON TRIHALIDES OR TITANIUM TETRAHALIDES - A CONVENIENT SYNTHESIS OF ALKYL-HALIDES FROM ALKYL FLUORIDES [J].

NAMAVARI, M ;

SATYAMURTHY, N ;

BARRIO, JR .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 72 (01) :89-93