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指导小组参与苄位 C(sp)-H/C(sp)-H 交叉脱氢偶联(CDC):氮杂多环的合成。

Directing Group Participated Benzylic C(sp)-H/C(sp)-H Cross-Dehydrogenative Coupling (CDC): Synthesis of Azapolycycles.

机构信息

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University , Nanjing 211816, China.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637616, Singapore.

出版信息

Org Lett. 2018 Feb 2;20(3):652-655. doi: 10.1021/acs.orglett.7b03748. Epub 2018 Jan 12.

Abstract

An efficient method to construct azapolycycles via directing group participated benzylic C(sp)-H/C(sp)-H cross-dehydrogenative coupling reactions is described. The reaction proceeded through a palladium catalyzed C(sp)-H activation followed by coupling with a C(sp)-H bond of quinoline to afford the azapolycyclic compounds. The reaction works with a broad substrate scope affording the products in moderate to good yields with excellent diastereoselectivities. Control experiments further supported the proposed mechanism.

摘要

描述了一种通过导向基团参与的苄基 C(sp)-H/C(sp)-H 交叉脱氢偶联反应构建氮杂多环的有效方法。该反应通过钯催化的 C(sp)-H 活化,然后与喹啉的 C(sp)-H 键偶联进行,得到氮杂多环化合物。该反应具有广泛的底物范围,中等至良好的产率和优异的非对映选择性。控制实验进一步支持了所提出的机理。

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