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J Am Chem Soc. 2008 Mar 5;130(9):2771-3. doi: 10.1021/ja710864p. Epub 2008 Feb 12.
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Recent Pat Anticancer Drug Discov. 2006 Jun;1(2):163-70. doi: 10.2174/157489206777442205.
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Investigations on the Suzuki-Miyaura and Negishi couplings with alkenyl phosphates: application to the synthesis of 1,1-disubstituted alkenes.关于铃木-宫浦反应和根岸偶联反应与链烯基磷酸酯的研究：在1,1-二取代烯烃合成中的应用。
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Insights into the mechanism of the Negishi reaction: ZnRX versus ZnR2 reagents.
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Alkyl-fluorinated thymidine derivatives for imaging cell proliferation II. Synthesis and evaluation of N3-(2-[18F]fluoroethyl)-thymidine.用于细胞增殖成像的烷基氟化胸苷衍生物II. N3-(2-[18F]氟乙基)-胸苷的合成与评价
Nucl Med Biol. 2006 Aug;33(6):765-72. doi: 10.1016/j.nucmedbio.2006.06.001.
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Nucl Med Biol. 2006 Aug;33(6):751-64. doi: 10.1016/j.nucmedbio.2006.06.003.
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Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides.通过将锌直接插入有机碘化物和溴化物中来高效合成功能化有机锌化合物。
Angew Chem Int Ed Engl. 2006 Sep 11;45(36):6040-4. doi: 10.1002/anie.200601450.
8
Imaging herpes viral thymidine kinase-1 reporter gene expression with a new 18F-labeled probe: 2'-fluoro-2'-deoxy-5-[18F]fluoroethyl-1-beta-d-arabinofuranosyl uracil.用新型18F标记探针成像疱疹病毒胸苷激酶-1报告基因表达：2'-氟-2'-脱氧-5-[18F]氟乙基-1-β-D-阿拉伯呋喃糖基尿嘧啶。
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The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst.首次利用钯-氮杂环卡宾（NHC）催化剂实现两个烷基中心的根岸交叉偶联反应。
Org Lett. 2005 Aug 18;7(17):3805-7. doi: 10.1021/ol0514909.

通过根岸交叉偶联反应合成5-氟烷基化嘧啶核苷。

Synthesis of 5-fluoroalkylated pyrimidine nucleosides via Negishi cross-coupling.

作者信息

Chacko Ann-Marie, Qu Wenchao, Kung Hank F

机构信息

Department of Pharmacology, University of Pennsylvania, 3700 Market Street, Suite 305, Philadelphia, Pennsylvania 19104, USA.

出版信息

J Org Chem. 2008 Jul 4;73(13):4874-81. doi: 10.1021/jo800444y. Epub 2008 Jun 4.

DOI:10.1021/jo800444y
PMID:18522415
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4122541/
Abstract

5-Fluoroalkylated pyrimidine nucleosides (1) have potential as therapeutic agents and molecular imaging agents targeting HSV1-tk suicide gene therapy. Thus, straightforward preparation of 5-fluoroalkylated nucleoside derivatives has been developed. Reported herein are the first examples of Pd-catalyzed Negishi cross-coupling of 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine (2a) and 3-N-benzoyl-3',5'-di-O-benzoyl-5-iodo-2'-deoxy-2'-fluoroarabinouridine (2b) with unactivated Csp(3) fluoroalkylzinc bromides. This paper demonstrates the first synthesis of six 5-fluoroalkyl-2'-deoxypyrimidine nucleoside derivatives with three to five methylene chain lengths (5). Furthermore, this methodology has been extended to create a series of 13 5-alkyl-substituted nucleosides, including the target nucleosides 5 and 5-silyloxypropyl and 5-cyanobutyl derivatives.

摘要

5-氟烷基化嘧啶核苷（1）有潜力作为靶向单纯疱疹病毒1型胸苷激酶自杀基因疗法的治疗剂和分子成像剂。因此，已开发出5-氟烷基化核苷衍生物的直接制备方法。本文报道了首例钯催化的3-N-苯甲酰基-3',5'-二-O-苯甲酰基-5-碘-2'-脱氧尿苷（2a）和3-N-苯甲酰基-3',5'-二-O-苯甲酰基-5-碘-2'-脱氧-2'-氟阿拉伯糖核苷（2b）与未活化的Csp(3)氟烷基溴化锌的根岸交叉偶联反应。本文展示了首例六个具有三至五个亚甲基链长度的5-氟烷基-2'-脱氧嘧啶核苷衍生物（5）的合成。此外，该方法已扩展用于制备一系列13种5-烷基取代核苷，包括目标核苷5以及5-硅氧基丙基和5-氰基丁基衍生物。