Sustainable vanadium(V)-catalyzed oxybromination of styrene: Two-phase system versus ionic liquids

被引：39

作者：

Conte, V ^{[1
]}

Floris, B ^{[1
]}

Galloni, P ^{[1
]}

Silvagni, A ^{[1
]}

机构：

[1] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy

来源：

PURE AND APPLIED CHEMISTRY | 2005年 / 77卷 / 09期

关键词：

vanadium; hydrogen peroxide; oxidation; ionic liquids; styrene; oxybromination;

D O I：

10.1351/pac200577091575

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxybromination reaction of styrene was performed in a two-phase system of water/ionic liquids (ILs). The aim of the work was to make the mild and efficient two-phase system previously developed for the vanadium(V)-catalyzed oxybromination of alkenes, inspired by the activity of haloperoxidase enzymes, even more interesting from a sustainable point of view. As in that case, a brominating intermediate was formed from the metal catalyst, H2O2, and bromide ion in the acid aqueous phase, but chlorinated solvents were replaced with ILs. [bmim(+)][PF6-], [bm(2)im(+)][PF6-], [bmim(+)][BF4-] [bmim(+)][CF3SO3-], and [bmim(+)][(CF3SO2)(2)N-] were tested. We report on interesting results in terms of reaction rates and selectivities.

引用

页码：1575 / 1581

页数：7

共 27 条

[1] VANADIUM BROMOPEROXIDASES MIMICKING SYSTEMS - BROMOHYDRINS FORMATION AS EVIDENCE OF THE OCCURRENCE OF A HYPOBROMITE-LIKE VANADIUM COMPLEX [J].

ANDERSSON, M ;

CONTE, V ;

DIFURIA, F ;

MORO, S .

TETRAHEDRON LETTERS, 1995, 36 (15) :2675-2678

[2] Electrospray behavior of lacunary Keggin-type polyoxotungstates [XW11O39]p- (X = Si, P):: Mass spectrometric evidence for a concentration-dependent incorporation of an MOn+ (M = WVI, MoVI, VV) unit into the polyoxometalate vacancy [J].

Bonchio, M ;

Bortolini, O ;

Conte, V ;

Sartorel, A .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (04) :699-704

[3] FRIEDEL CRAFTS REACTIONS IN AMBIENT-TEMPERATURE MOLTEN-SALTS [J].

BOON, JA ;

LEVISKY, JA ;

PFLUG, JL ;

WILKES, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :480-483

[4]

Bortolini O, 1999, EUR J ORG CHEM, V1999, P3237

[5]

Butler A, 1997, STRUCT BOND, V89, P109

[6] Mechanistic considerations of the vanadium haloperoxidases [J].

Butler, A .

COORDINATION CHEMISTRY REVIEWS, 1999, 187 :17-35

[7]

Cammarata L, 2001, PHYS CHEM CHEM PHYS, V3, P5192, DOI 10.1039/b106900d

[8]

Chauvin Y, 1995, ANGEW CHEM INT EDIT, V34, P2698

[9]

Chiappe C, 2002, EUR J ORG CHEM, V2002, P2831

[10] Models for the active site of vanadium-dependent haloperoxidases: insight into the solution structure of peroxo vanadium compounds [J].

Conte, V ;

Bortolini, O ;

Carraro, M ;

Moro, S .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2000, 80 (1-2) :41-49

← 1 2 3 →