Synthesis and structural characterization of N-heterocyclic carbene complexes of silver(I) and rhodium(I) from caffeine

被引:111
作者
Kascatan-Nebioglu, A [1 ]
Panzner, MJ [1 ]
Garrison, JC [1 ]
Tessier, CA [1 ]
Youngs, WJ [1 ]
机构
[1] Univ Akron, Dept Chem, Akron, OH 44325 USA
关键词
D O I
10.1021/om030689r
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The imidazolium cation 1,3,7,9-tetramethylxanthinium methyl sulfate (1a) is obtained by the reaction of caffeine with dimethyl sulfate. The anion exchange of la gives 1,3,7,9-tetramethylxanthinium hexafluorophosphate (1b). Ligand la reacts with Ag2O in water to yield an N-heterocyclic carbene (NHC) silver(I) complex (2a). Similarly, ligand 1b, reacts with Ag2O in DMSO to yield NHC silver(I) complex 2b in high yield. A carbene transfer reaction of 2b with [Rh(COD)Cl](2) gives NHC Rh(I) complex 3. All compounds were characterized by H-1 NMR, C-13 NMR, and mass spectrometry. The solid-state structures of 1b, 2b, and 3 were determined by X-ray crystallography.
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收藏
页码:1928 / 1931
页数:4
相关论文
共 30 条
[1]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[2]   HOMOLEPTIC CARBENE SILVER(I) AND CARBENE COPPER(I) COMPLEXES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
CALABRESE, JC ;
DAVIDSON, F .
ORGANOMETALLICS, 1993, 12 (09) :3405-3409
[3]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[4]   SYNTHESEN IN DER PURINREIHE .15. SYNTHESEN VON XANTHINIUM- UND GUANINIUM-BETAINEN [J].
BREDERECK, H ;
KOSER, W ;
SCHELLENBERG, P ;
CHRISTMANN, O ;
NAST, R .
CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (07) :1812-&
[5]   Rhodium carbene complexes: Highly selective catalysts for the hydroformylation of styrene derivatives [J].
Chen, AC ;
Ren, L ;
Decken, A ;
Crudden, CM .
ORGANOMETALLICS, 2000, 19 (18) :3459-3461
[6]   Rhodium and iridium complexes of N-heterocyclic carbenes via transmetalation: Structure and dynamics [J].
Chianese, AR ;
Li, XW ;
Janzen, MC ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2003, 22 (08) :1663-1667
[7]   NITROGEN-BOUND AND CARBON-BOUND XANTHINE COMPLEXES OF RUTHENIUM AMMINES [J].
CLARKE, MJ ;
TAUBE, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1397-1403
[8]  
COLACIORODRIGUE.E, 1984, ANAL QUIM B, V80, P49
[9]   Preparation of metal-imidazolidin-2-ylidene complexes by oxidative addition [J].
Fürstner, A ;
Seidel, G ;
Kremzow, D ;
Lehmann, CW .
ORGANOMETALLICS, 2003, 22 (05) :907-909
[10]   Synthesis and structural characterization of an imidazolium-linked cyclophane and the silver complex of an N-heterocyclic carbene-linked cyclophane [J].
Garrison, JC ;
Simons, RS ;
Talley, JM ;
Wesdemiotis, C ;
Tessier, CA ;
Youngs, WJ .
ORGANOMETALLICS, 2001, 20 (07) :1276-1278