Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds

被引：277

作者：

Scott, VJ ^{[1
]}

Çelenligil-Çetin, R ^{[1
]}

Ozerov, OV ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 09期

关键词：

D O I：

10.1021/ja0426138

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Room-temperature catalytic hydrodefluorination of the strong C(sp3)-F bonds in benzotrifluorides and fluoropentane is catalyzed by Et3Si[B(C6F5)4] and uses Et3SiH as the source of H. Ar-CF3 compounds are converted to Ar-CH3 and fluropentane to pentane. The reaction is thought to proceed via abstraction of F- by Et3Si[B(C6F5)4], and the substituent effects are consistent with this hypothesis. Copyright © 2005 American Chemical Society.

引用

收藏

页码：2852 / 2853

页数：2

相关论文

共 44 条

[1] HOMOGENEOUS METAL-CATALYZED HYDROGENOLYSIS OF C-F BONDS [J].

AIZENBERG, M ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) :8674-8675

[2] CATALYTIC ACTIVATION OF CARBON-FLUORINE BONDS BY A SOLUBLE TRANSITION-METAL COMPLEX [J].

AIZENBERG, M ;

MILSTEIN, D .

SCIENCE, 1994, 265 (5170) :359-361

[3]

[Anonymous], CHEM ORGANIC FLUORIN

[4] STABLE SILYLNITRILIUM IONS [J].

BAHR, SR ;

BOUDJOUK, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4514-4519

[5] ETA(2)-COORDINATION AND C-F ACTIVATION OF HEXAFLUOROBENZENE BY CYCLOPENTADIENYLRHODIUM AND CYCLOPENTADIENYLIRIDIUM COMPLEXES [J].

BELT, ST ;

HELLIWELL, M ;

JONES, WD ;

PARTRIDGE, MG ;

PERUTZ, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1429-1440

[6] Routes to fluorinated organic derivatives by nickel mediated C-F activation of heteroaromatics [J].

Braun, T ;

Perutz, RN .

CHEMICAL COMMUNICATIONS, 2002, (23) :2749-2757

[7] Recent advances in C-F bond activation [J].

Burdeniuc, J ;

Jedlicka, B ;

Crabtree, RH .

CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (02) :145-154

[8] Defluorination of perfluoropropene using CP*2ZrH2 and CP*2ZrHF:: A mechanism investigation from a joint experimental-theoretical perspective [J].

Clot, E ;

Mégret, C ;

Kraft, BM ;

Eisenstein, O ;

Jones, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5647-5653

[9] INTRAMOLECULAR ACTIVATION OF A C-F BOND AT PLATINUM(II) IN THE PRESENCE OF WEAKER C-X BONDS (X = H, CL AND BR) [J].

CRESPO, M ;

MARTINEZ, M ;

SALES, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (11) :822-823

[10] Rapid intermolecular carbon-fluorine bond activation of pentafluoropyridine at nickel(0): Comparative reactivity of fluorinated arene and fluorinated pyridine derivatives [J].

Cronin, L ;

Higgitt, CL ;

Karch, R ;

Perutz, RN .

ORGANOMETALLICS, 1997, 16 (22) :4920-4928

← 1 2 3 4 5 →