W(II)-catalyzed hydroarylation of bicyclo[2.2.1]-hept-2-ene by simple arenes

被引:12
作者
Malinowska, A [1 ]
Czelusniak, I [1 ]
Górski, M [1 ]
Szymanska-Buzar, T [1 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
关键词
hydroarylation; tungsten(II) catalyst; norbornene; C-C bond formation; C-H bond activation;
D O I
10.1016/j.tetlet.2005.01.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tungsten(II) carbonyl compound (CO)(4)W(mu-Cl)(3)W(SnCl3)(CO)(3) has been found to be a very effective catalyst for the hydroarylation of bicyclo[2.2.1]hept-2-ene (norbornene) conducted in arene solution at room temperature. Norbornene adducts with benzene, toluene, para-xylene, and mesitylene have been isolated and their structures have been unambiguously established by means of H-1 and C-13 NMR spectroscopy. On the basis of H-1 NMR monitoring of several catalytic reactions, a possible mechanism involving coordination of norbornene to the W(II) atom and its activation has been proposed. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1427 / 1431
页数:5
相关论文
共 45 条
[1]   SUBSTITUENT CHEMICAL-SHIFTS IN NMR .4. - H-1 SCS IN SOME 2-SUBSTITUTED NORBORNANES AND BORNANES [J].
ABRAHAM, RJ ;
BARLOW, AP ;
ROWAN, AE .
MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (11) :1074-1084
[2]   C-H activation of substituted arenes by tungsten alkylidene complexes: Products, selectivity, and mechanism [J].
Adams, CS ;
Legzdins, P ;
Tran, E .
ORGANOMETALLICS, 2002, 21 (07) :1474-1486
[3]   PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON [J].
ARCADI, A ;
MARINELLI, F ;
BERNOCCHI, E ;
CACCHI, S ;
ORTAR, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) :249-256
[4]   STEREOCHEMISTRY OF PENTACYCLO[8.2.1.14,7.O2,9.O3,8]TETRADECANES AND -DIENES . NORBORNENE AND NORBORNADIENE DIMERS [J].
ARNOLD, DR ;
TRECKER, DJ ;
WHIPPLE, EB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (12) :2596-&
[5]   REACTION OF OPTICALLY-ACTIVE EXO-2-BROMONORBORNANE AND ENDO-2-BROMONORBORNANE WITH NITRONIUM TETRAFLUOROBORATE IN ACETONITRILE - EVIDENCE FOR A CARBENIUM ION PATHWAY [J].
BACH, RD ;
HOLUBKA, JW ;
TAAFFEE, TH .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 44 (01) :35-38
[6]   Theoretical investigation of C-H/olefin coupling catalyzed by zirconium(IV) complexes [J].
Bi, SW ;
Lin, ZY ;
Jordan, RF .
ORGANOMETALLICS, 2004, 23 (21) :4882-4890
[7]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .17. SOLVOLYSIS OF PARA-2-NORBORNYL-TERT-CUMYL CHLORIDES - SIGMA+ CONSTANTS FOR PARA EXO-NORBORNYL AND PARA EXO-ENDO-NORBORNYL AND QUESTION OF AN UNUSUAL POLARIZABILITY OF SIGMA-BONDS IN 2-NORBORNYL GROUP [J].
BROWN, HC ;
GNEDIN, BG ;
TAKEUCHI, K ;
PETERS, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :610-613
[8]   Palladium-arene interactions in catalytic intermediates:: An experimental and theoretical investigation of the soft rearrangement between η1 and η2 coordination modes [J].
Catellani, M ;
Mealli, C ;
Motti, E ;
Paoli, P ;
Perez-Carreño, E ;
Pregosin, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4336-4346
[9]   CONTROL OF ETA(2)-COORDINATION VS C-H BOND ACTIVATION BY RHODIUM - THE ROLE OF AROMATIC RESONANCE ENERGIES [J].
CHIN, RM ;
DONG, LZ ;
DUCKETT, SB ;
PARTRIDGE, MG ;
JONES, WD ;
PERUTZ, RN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) :7685-7695
[10]   Ring-opening metathesis polymerization of norbornene and norbornadiene by tungsten(II) and molybdenum(II) complexes [J].
Czelusniak, I ;
Szymanska-Buzar, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 190 (1-2) :131-143