A Versatile Methodology for the Regioselective C8-Metalation of Purine Bases

被引：86

作者：

Brackemeyer, Dirk ^{[1
]}

Herve, Alexandre ^{[1
]}

Brinke, Christian Schulte To ^{[1
]}

Jahnke, Mareike C. ^{[1
]}

Hahn, F. Ekkehardt ^{[1
]}

机构：

[1] Univ Munster, Inst Anorgan & Analyt Chem, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 22期

关键词：

C-H ARYLATION; CATIONIC CYCLIC CARBENE; OXIDATIVE ADDITION; HETEROCYCLIC CARBENES; BOND FORMATION; COMPLEXES; METAL; FUNCTIONALIZATION; DERIVATIVES; PALLADIUM(II);

D O I：

10.1021/ja5030904

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Purine nucleobases are excellent ligands for metal ions, forming normally coordinative Werner-type bonds by utilizing the N donor atoms of the nucleobase skeleton. Here we show that purines such as 8-chlorocaffeine and 8-bromo-9-methyladenine react with [Pt(PPh3)(4)] under oxidative addition of the C-8-halogen bond to the metal center. The resulting Pt-II complexes feature a C-8-bound ylidene ligand. Protonation of the ylidene at the N-7/9-atom yields complexes bearing a protic N-heterocyclic carbene ligand derived from the purine base with an NMe,NH-substitution pattern.

引用

页码：7841 / 7844

页数：4

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