Ruthenium-oxo and -tosylimido porphyrin complexes for epoxidation and aziridination of alkenes

被引：56

作者：

Che, CM ^{[1
]}

Yu, WY ^{[1
]}

机构：

[1] Univ Hong Kong, Dept Chem, Pokfulam Rd, Hong Kong, Peoples R China

来源：

PURE AND APPLIED CHEMISTRY | 1999年 / 71卷 / 02期

关键词：

D O I：

10.1351/pac199971020281

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dioxoruthenium(VI) porphyrins including those containing chiral porphyrinato ligands can be readily prepared by oxidation of [Ru-II(Por)(CO)(MeOH)] with PhIO or metachloroperoxybenzoic acid. Similar reactions with PhINTs gave [Ru-VI(Por)(NTs)(2)] isolated as air stable solids at room temperature. The [Ru-VI(Por)O-2] complexes are competent oxidants for epoxidation of alkenes with high selectivities. Enantioselective epoxidation of alkenes giving the corresponding organic epoxides with moderate to good enantioselectivites have also been achieved using chiral [Ru-VI(D-4-Por*)O-2] [D-4-H(2)Por* = 5 10,15,20-tetrakis-(1S,4R,5R,8S-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl)porphyrin] and [Ru-VI(D-2-Por*)O-2] complexes. The mechanism of alkene epoxidation by [Ru-VI(Por)O-2] has been examined. Procedures for catalytic epoxidation of alkenes using ruthenium porphyrin catalysts has also been developed. [Ru-VI(Por)(NTs)(2)] was found to undergo aziridination of alkenes and amidation of alkanes in organic solvents at room temperature.

引用

页码：281 / 288

页数：8

共 39 条

[1] Synthesis, characterisation and reactivity of novel bis(tosyl)imidoruthenium(VI) porphyrin complexes; X-ray crystal structure of a tosylamidoruthenium(IV) porphyrin [J].

Au, SM ;

Fung, WH ;

Cheng, MC ;

Che, CM ;

Peng, SM .

CHEMICAL COMMUNICATIONS, 1997, (17) :1655-1656

[2] A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES [J].

BECK, JS ;

VARTULI, JC ;

ROTH, WJ ;

LEONOWICZ, ME ;

KRESGE, CT ;

SCHMITT, KD ;

CHU, CTW ;

OLSON, DH ;

SHEPPARD, EW ;

MCCULLEN, SB ;

HIGGINS, JB ;

SCHLENKER, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10834-10843

[3] CATALYTIC ENANTIOSELECTIVE EPOXIDATIONS OF SIMPLE OLEFINS [J].

BOLM, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (04) :403-404

[4] KINETICS OF ALKENE OXIDATION BY CATIONIC TRANS-DIOXO-RUTHENIUM(VI) COMPLEXES - EFFECT OF DRIVING FORCE ON RATE CONSTANTS [J].

CHE, CM ;

LI, CK ;

TANG, WT ;

YU, YY .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (21) :3153-3158

[5] METAL-LIGAND MULTIPLE BONDS - OXO, IMIDO AND NITRIDO COMPLEXES OF RUTHENIUM AND OSMIUM [J].

CHE, CM .

PURE AND APPLIED CHEMISTRY, 1995, 67 (02) :225-232

[6] HIGH-VALENT COMPLEXES OF RUTHENIUM AND OSMIUM [J].

CHE, CM ;

YAM, VWW .

ADVANCES IN INORGANIC CHEMISTRY, 1992, 39 :233-325

[7]

CHE CM, 1996, ADV TRANSIT MET COOR, V1, P209

[8] BIS(ALKOXY)RUTHENIUM(IV) PORPHYRIN COMPLEXES AND AEROBIC OXIDATION OF ALCOHOLS [J].

CHENG, SYS ;

RAJAPAKSE, N ;

RETTIG, SJ ;

JAMES, BR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2669-2670

[9] A KINETIC-STUDY ON THE REACTIVITY OF A CIS-DIOXORUTHENIUM(VI) COMPLEX - OXIDATION OF ALCOHOLS, AROMATIC-HYDROCARBONS, AND ALKENES BY CIS-[RU-VI(TET-ME(6))O-2](2+) [J].

CHENG, WC ;

YU, WY ;

LI, CK ;

CHE, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6840-6846

[10] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].

EVANS, DA ;

FAUL, MM ;

BILODEAU, MT ;

ANDERSON, BA ;

BARNES, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329

← 1 2 3 4 →