Silver-Free Palladium-Catalyzed C(sp3)-H Arylation of Saturated Bicyclic Amine Scaffolds.
Silver-Free Palladium-Catalyzed C(sp3)-H Arylation of Saturated Bicyclic Amine Scaffolds.
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DOI：
10.1021/acs.joc.7b02665
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发表时间：
2017-12
期刊：
影响因子：
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通讯作者：
C. Coomber;L. Benhamou;Dejan-Krešimir Bučar;Peter D. Smith;M. Porter;T. Sheppard
中科院分区：
文献类型：
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作者：
C. Coomber;L. Benhamou;Dejan-Krešimir Bučar;Peter D. Smith;M. Porter;T. Sheppard
在这里，我们报道了一种无银Pd(II)催化的饱和双环胺和三环胺骨架的C(SP3)-H芳基化反应。该反应使用了一系列芳基碘和芳基溴化物，包括含醛、酮、酯、游离酚和杂环的官能化实例，提供了良好的产率。该方法已应用于与医学相关的支架。合成并表征了催化循环中的两种中间体钯配合物，并提出了反应机理。在相对温和的条件下，导向基团的去除取得了良好的产率。
Herein, we report a silver-free Pd(II)-catalyzed C(sp3)-H arylation of saturated bicyclic and tricyclic amine scaffolds. The reaction provides good yields using a range of aryl iodides and aryl bromides including functionalized examples bearing aldehydes, ketones, esters, free phenols, and heterocycles. The methodology has been applied to medicinally relevant scaffolds. Two of the intermediate palladium complexes in the catalytic cycle have been prepared and characterized, and a mechanism is proposed. Removal of the directing group proceeded with good yield under relatively mild conditions.