Regioselective arylation of 2′-deoxyribonucleosides on amido or imino sites by copper(II)-mediated direct coupling with arylboronic acids

被引：13

作者：

Dai, Q ^{[1
]}

Ran, CZ ^{[1
]}

Harvey, RG ^{[1
]}

机构：

[1] Univ Chicago, Ben May Inst Canc Res, Chicago, IL 60637 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 08期

关键词：

N '-aryl-2 '-deoxyguanosine; arylation of nucleosides; arylboronic acids; copper-mediated coupling of amides and imides;

D O I：

10.1016/j.tet.2005.11.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-1-Aryl derivatives of 2'-deoxyguanosine (dG) were synthesized by copper(II)-mediated coupling of dG with arylboronic acids. Analogous aryl derivatives of 2'-deoxyinosine (dIn), 2'-deoxyuridine (dU), thymidine (T), 2'-deoxyadenosine (dA), and 2'-deoxycytidine (dC) were also conveniently synthesized by this method. Arylation took place preferentially on the amido functions in dG and dIn and the imino functions in dU or T. Remarkably, the nucleosides themselves served as internal ligands as well as reactants. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1764 / 1771

页数：8

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