Ngassa Felix N, Dekorver Kyle A, Melistas Theothora S, Yeh Edmund A-H, Lakshman Mahesh K
Department of Chemistry, Grand Valley State University, Allendale, Michigan 49401, USA.
Org Lett. 2006 Sep 28;8(20):4613-6. doi: 10.1021/ol0619516.
Direct arylation of the exocyclic amino groups of nucleosides represents a simple approach to N-aryl nucleoside derivatives. To date, one limitation has been that only electron-deficient aryl bromides and triflates possessed adequate reactivity for efficient, direct N-arylation of nucleosides. We demonstrate herein that Pd-Xantphos catalytic systems lead to successful N-arylation of suitably protected 2'-deoxyadenosine and 2'-deoxyguanosine with a wide range of aryl bromides.
核苷外环氨基的直接芳基化是制备N-芳基核苷衍生物的一种简单方法。迄今为止，一个限制是只有缺电子的芳基溴化物和三氟甲磺酸酯对核苷的高效直接N-芳基化具有足够的反应活性。我们在此证明，钯-联二萘酚膦催化体系能够使多种芳基溴化物与适当保护的2'-脱氧腺苷和2'-脱氧鸟苷成功进行N-芳基化反应。
