Vinylic C-F bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconocene

被引：55

作者：

Fujiwara, M ^{[1
]}

Ichikawa, J ^{[1
]}

Okauchi, T ^{[1
]}

Minami, T ^{[1
]}

机构：

[1] Kyushu Inst Technol, Dept Appl Biochem, Kitakyushu, Fukuoka 8048550, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 40期

关键词：

coupling reactions; fluorine; fluorine compounds; olefins; zirconium; zirconium compounds;

D O I：

10.1016/S0040-4039(99)01491-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(p-2,2-Difluorovinyloxyphenyl)dimethylamine, readily obtained from 2,2,2-trifluoroethanol, is treated with zirconocene equivalent 'Cp2Zr' to generate thermostable 1-fluorovinylzirconocene via a C-F bond cleavage. This 1-fluorovinylzirconocene can be used for C-C bond formation through the cross-coupling with aryl iodides in the presence of palladium catalyst and zinc iodide, leading to (Z)-1-aryl-2-(p-dimethylaminophenoxy)-1-fluoroolrfins in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7261 / 7265

页数：5

共 28 条

[1] Remarkable regioselectivity in the reaction between [(η5-C5Me4H)RhCl(μ-Cl)]2 and (C6F5)2PCH2CH2P(C6F5)2:: synthesis of a chiral-at-metal rhodium complex cation via carbon-fluorine and -hydrogen bond activation and carbon-carbon bond formation [J].