Synthesis of PdII Complexes Bearing pNHC Ligands by Oxidative Addition of 8-Halogenotheophyllines and 8-Bromoadenine to Pd0

被引:14
作者
Blumenberg, Jonas [1 ]
Wilm, Lukas F. B. [1 ]
Hahn, F. Ekkehardt [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Inst Anorgan & Analyt Chem, D-48149 Munster, Germany
关键词
N-HETEROCYCLIC CARBENES; PALLADIUM(II); METALATION; STABILITY;
D O I
10.1021/acs.organomet.0c00046
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Various 8-halogenotheophyllines (halogen = CI, Br, I) were selectively C8 metalated by an oxidative addition of the C8- halogen bond to [Pd(PPh3)(4)] to give the Pd-II azolato complexes [1]-[3]. The complexes were protonated at the N9 nitrogen atom to yield the NH,NH-NHC (pNHC) complexes [4]BF4 -[6]BF4. Due to the unsymmetrical nature of the backbone of the theophylline-derived pNHC ligands, two NH resonances were observed by H-1 NMR spectroscopy. In addition, 8-bromoadenine was also regioselectively C8 metalated via an oxidative addition of the C8-Br bond to [Pd(PPh3)(4)] in the presence of the proton source pyridinium tetrafluoroborate to give [7]BF4.
引用
收藏
页码:1281 / 1287
页数:7
相关论文
共 39 条
[1]   A HIGHLY PROPELLER-TWISTED ADENINE-ADENINE BASE PAIR IN 8-TERT-BUTYLADENINE [J].
ALEXANDRESCU, A ;
DRENDEL, WB ;
SUNDARALINGAM, M .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :1041-1044
[2]   Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].
Amyes, TL ;
Diver, ST ;
Richard, JP ;
Rivas, FM ;
Toth, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374
[3]   Isolation and interconversion of protic N-heterocyclic carbene and imidazolyl complexes:: Application to catalytic dehydrative condensation of N-(2-pyridyl)benzimidazole and allyl alcohol [J].
Araki, Kenjirou ;
Kuwata, Shigeki ;
Ikariya, Takao .
ORGANOMETALLICS, 2008, 27 (10) :2176-2178
[4]   A Self-Complementary Nucleoside: Synthesis, Solid-State Structure, and Fluorescence Behavior [J].
Bang, Eun-Kyoung ;
Won, Jiyeon ;
Moon, Dohyun ;
Lee, Jin Yong ;
Kim, Byeang Hyean .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (08) :2047-2053
[5]   Site-selective metallation of dicarbene precursors [J].
Bente, Stefanie ;
Kampert, Florian ;
Tan, Tristan T. Y. ;
Hahn, F. Ekkehardt .
CHEMICAL COMMUNICATIONS, 2018, 54 (91) :12887-12890
[6]   Caffeine-Based Gold(I) N-Heterocyclic Carbenes as Possible Anticancer Agents: Synthesis and Biological Properties [J].
Bertrand, Benoit ;
Stefan, Loic ;
Pirrotta, Marc ;
Monchaud, David ;
Bodio, Ewen ;
Richard, Philippe ;
Le Gendre, Pierre ;
Warmerdam, Elena ;
de Jager, Marina H. ;
Groothuis, Geny M. M. ;
Picquet, Michel ;
Casini, Angela .
INORGANIC CHEMISTRY, 2014, 53 (04) :2296-2303
[7]   AN EMPIRICAL CORRECTION FOR ABSORPTION ANISOTROPY [J].
BLESSING, RH .
ACTA CRYSTALLOGRAPHICA SECTION A, 1995, 51 :33-38
[8]   A Versatile Methodology for the Regioselective C8-Metalation of Purine Bases [J].
Brackemeyer, Dirk ;
Herve, Alexandre ;
Brinke, Christian Schulte To ;
Jahnke, Mareike C. ;
Hahn, F. Ekkehardt .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) :7841-7844
[9]   C-H and N-H activation by Pt(0) in N- and O-heteroaromatic compounds [J].
Chantson, JT ;
Lotz, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (07) :1315-1324
[10]   Regioselective N- and C-Metalation of Neutral 2-Halogenobenzimidazole Derivatives [J].
Das, Rajorshi ;
Blumberg, Jonas ;
Daniliuc, Constantin G. ;
Schnieders, David ;
Neugebauer, Johannes ;
Han, Ying-Feng ;
Hahn, F. Ekkehardt .
ORGANOMETALLICS, 2019, 38 (17) :3278-3285