Synlett 2019; 30(14): 1688-1692
DOI: 10.1055/s-0039-1690103
cluster
© Georg Thieme Verlag Stuttgart · New York

Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide

Huimin Li
,
Lihao Liao
,
Xiaodan Zhao
We thank the National Natural Science Foundation of China (Grant Nos. 21772239 and 91856109), and the Natural Science Foundation of Guangdong Province (Grant No. 2014A030312018) for financial support.
Further Information

Publication History

Received: 30 April 2019

Accepted after revision: 07 June 2019

Publication Date:
28 June 2019 (online)

Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.

Supporting Information

 
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