Activation of alkyl halides via a silver-catalyzed carbene insertion process

被引：132

作者：

Dias, HVR ^{[1
]}

Browning, RG ^{[1
]}

Polach, SA ^{[1
]}

Diyabalanage, HVK ^{[1
]}

Lovely, CJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 31期

关键词：

D O I：

10.1021/ja034801o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The silver complex [HB(3,5-(CF3)2Pz)3]Ag(THF) featuring a highly fluorinated tris(pyrazolyl)borate ligand catalyzes the formation of aliphatic carbon-halogen bond activation products under remarkably mild conditions. For example, the reaction between CHCl3 and ethyl diazoacetate (EDA) at room temperature in the presence of the silver catalyst afforded HClC(CO2Et)CCl2H in 60% yield. The presence of β-hydrogens on the alkyl halide leads to net hydrogen halide addition to the carbene and an alkene. Copyright © 2003 American Chemical Society.

引用

页码：9270 / 9271

页数：2

共 27 条

[1] Investigation of silver salt metathesis: Preparation of cationic germanium(II) and tin(II) complexes, and silver adducts containing unsupported silver-germanium and silver-tin bonds [J].

Ayers, AE ;

Dias, HVR .

INORGANIC CHEMISTRY, 2002, 41 (12) :3259-3268

[2] Highly regioselective functionalization of aliphatic carbon-hydrogen bonds with a perbromohomoscorpionate copper(I) catalyst [J].

Caballero, A ;

Díaz-Requejo, MM ;

Belderraín, TR ;

Nicasio, MC ;

Trofimenko, S ;

Pérez, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1446-1447

[3]

Dias HVR, 2000, INORG CHEM, V39, P4676

[4] Low-valent gallium, indium, and tin compounds that contain a highly fluorinated tris(pyrazolyl)borate ligand:: Syntheses and characterization of [HB(3,5-(CF3)2Pz)3]Ga, [HB(3,5-(CF3)2Pz)3]In, and [HB(3,5-(CF3)2Pz)3]Sn(CF3SO3) [J].

Dias, HVR ;

Jin, WC .

INORGANIC CHEMISTRY, 2000, 39 (04) :815-819

[5] Copper(I) ethylene adducts and aziridination catalysts based on fluorinated tris(pyrazolyl)borates [HB(3-(CF3),5-(R)PZ)3] (where R = CF3, C6H5, H; Pz = pyrazolyl) [J].

Dias, HVR ;

Lu, HL ;

Kim, HJ ;

Polach, SA ;

Goh, TKHH ;

Browning, RG ;

Lovely, CJ .

ORGANOMETALLICS, 2002, 21 (07) :1466-1473

[6] Synthesis and chemistry of [hydrotris(3,5-bis(trifluoromethyl)pyrazolyl)borato]silver(I) complexes [J].

Dias, HVR ;

Wang, ZY ;

Jin, WC .

INORGANIC CHEMISTRY, 1997, 36 (27) :6205-6215

[7] Monomeric indium(I) and silver(I) complexes of a polyfluorinated tris(pyrazolyl)borate [J].

Dias, HVR ;

Jin, WC .

INORGANIC CHEMISTRY, 1996, 35 (01) :267-268

[8] Coinage metal carbonyls and isocyanides: Synthesis and characterization of the gold(I)complexes [HB(3,5-(CF3)(2)Pz)(3)]AuCO and [HB(3,5-(CF3)(2)Pz)(3)]AuCNBu(t) [J].

Dias, HVR ;

Jin, WC .

INORGANIC CHEMISTRY, 1996, 35 (12) :3687-3694

[9] SYNTHESIS AND STRUCTURE OF [HYDRIDOTRIS(3,5-BIS(TRIFLUOROMETHYL)PYRAZOYL)BORATO]POTASSIUM [J].

DIAS, HVR ;

LU, HL ;

RATCLIFF, RE ;

BOTT, SG .

INORGANIC CHEMISTRY, 1995, 34 (08) :1975-1976

[10]

DIAS HVR, UNPUB

← 1 2 3 →