C-H Activation Guided by Aromatic N-H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes
C-H Activation Guided by Aromatic N-H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes
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DOI：
10.1021/jo501465q
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发表时间：
2014-10-03
影响因子：
3.6
通讯作者：
Park, Jaiwook
中科院分区：
文献类型：
--
作者：
Gupta, Sreya;Han, Junghoon;Park, Jaiwook
由不同的苄基叠氮化合物在Ru催化下原位生成芳香族N-H-酮亚胺，然后在Rh催化下与炔烃进行环化反应，得到相应的异喹啉。与传统的芳香族NH酮胺的合成方法不同，我们的方案在温和和中性的条件下工作，这使得具有不同官能团的异喹啉的合成成为可能，如羰基、酯、烯基和醚基。此外，由α-叠氮醚生成的亚胺类化合物被成功地用于1-烷氧基异喹啉的合成。
Aromatic N-H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic NH ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from alpha-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.