Convenient preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium into chalcogen-chalcogen bonds. Application in the ring-opening of epoxides

被引：43

作者：

Dowsland, J ^{[1
]}

McKerlie, F ^{[1
]}

Procter, DJ ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 25期

关键词：

lanthanides; epoxides; sulfides; selenium and compounds; tellurium and compounds;

D O I：

10.1016/S0040-4039(00)00687-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convenient conditions are reported for the preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium metal into the chalcogen-chalcogen bond of disulfides, diselenides, and ditellurides. The resulting complexes have been found to transfer arylsulfanyl, -selenanyl, and -telluranyl groups to epoxides in a facile ring-opening reaction. The ytterbium(III) chalcogenolate complexes appear to perform a dual role in both activating the epoxide, due to their Lewis acidic nature, and supplying a nucleophile to the coordinated substrate. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4923 / 4927

页数：5

共 29 条

[1] LANTHANIDE THIOLATE COMPLEXES - SYNTHESIS OF [EU(N(SIME3)2)(MU-SBUT)]2,[GD(N(SIME3)2)(MU-SBUT)]2,[Y(N(SIME3)2)(MU-SBUT)]2 AND THE X-RAY CRYSTAL-STRUCTURE OF THE GD COMPLEX [J].

ASPINALL, HC ;

BRADLEY, DC ;

HURSTHOUSE, MB ;

SALES, KD ;

WALKER, NPC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1585-1586

[2] MECHANICAL ACTIVATION OF MAGNESIUM TURNINGS FOR THE PREPARATION OF REACTIVE GRIGNARD-REAGENTS [J].

BAKER, KV ;

BROWN, JM ;

HUGHES, N ;

SKARNULIS, AJ ;

SEXTON, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :698-703

[3] SAMARIUM(II) IODIDE PROMOTED RADICAL RING-OPENING REACTIONS OF CYCLOPROPYL KETONES [J].

BATEY, RA ;

MOTHERWELL, WB .

TETRAHEDRON LETTERS, 1991, 32 (43) :6211-6214

[4] ELECTRON-TRANSFER CHEMISTRY OF (ME5C5)2YB - CLEAVAGE OF DIORGANOPEROXIDE AND RELATED CHALCOGENIDES TO GIVE (ME5C5)2YB(ER)(L) (E = O, S, SE, OR TE - L = A LEWIS BASE) - CRYSTAL-STRUCTURE OF (ME5C5)2YB(TEPH)(NH3) [J].

BERG, DJ ;

ANDERSEN, RA ;

ZALKIN, A .

ORGANOMETALLICS, 1988, 7 (08) :1858-1863

[5]

CETINKAYA B, 1992, J CHEM SOC CHEM COMM, P932

[6] REDUCTIVE CLEAVAGE OF C-S BOND BY SAMARIUM DIIODIDE - A NOVEL METHOD FOR THE SYNTHESIS OF DISULFIDES AND THIOLESTERS [J].

JIA, XS ;

ZHANG, YM ;

ZHOU, XJ .

TETRAHEDRON LETTERS, 1994, 35 (47) :8833-8834

[7] Samarium(II)-mediated 4-exo trig ketyl-olefin cyclisation of unsaturated aldehydes.: A general, stereoselective synthesis of functionalised cyclobutanols [J].

Johnston, D ;

McCusker, CM ;

Procter, DJ .

TETRAHEDRON LETTERS, 1999, 40 (26) :4913-4916

[8] Samarium(II)-mediated 4-exo-trig cyclisations of unsaturated aldehydes.: A stereoselective approach to functionalised cyclobutanols [J].

Johnston, D ;

McCusker, CF ;

Muir, K ;

Procter, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :681-695

[9] A novel synthesis of benzyl sulfides and selenides via Sm/BiCl3 system in aqueous media [J].

Lu, GL ;

Zhang, YM .

SYNTHETIC COMMUNICATIONS, 1998, 28 (23) :4479-4484

[10] MONOCYCLOOCTATETRAENYL(THIOLATO)SAMARIUM(III) COMPLEXES FROM THE REACTION OF METALLIC SAMARIUM WITH CYCLOOCTATETRAENE AND DIARYLDISULFIDE - CRYSTAL-STRUCTURES OF [SM(MU-SPH)(C8H8)(THF)2]2 AND [(SM[MU-S(2,4,6-TRIISOPROPYLPHENYL)](C8H8)(THF))2] [J].

MASHIMA, K ;

NAKAYAMA, Y ;

KANEHISA, N ;

KAI, Y ;

NAKAMURA, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) :1847-1848

← 1 2 3 →