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Synthesis 2019; 51(12): 2515-2522
DOI: 10.1055/s-0037-1611807
DOI: 10.1055/s-0037-1611807
special topic
Ruthenium-Catalyzed Directed C(3)–H Olefination of N-Acetyl-1,2-dihydroisoquinolines: A Method to Achieve C3-Olefinated Isoquinolines
SERB-India (EMR/2016/004298/OC) and CSIR-India [02(205)/14/EMR-II] are gratefully acknowledged for the research funding.Further Information
Publication History
Received: 15 February 2019
Accepted after revision: 02 April 2019
Publication Date:
15 April 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/201912/lookinside/thumbnails/ss-2019-c0102-st_10-1055_s-0037-1611807-1.jpg)
§ Equal contribution
Published as part of the Special Topic Ruthenium in Organic Synthesis
Abstract
A unique approach to achieve regioselective C(3)–H olefination of isoquinolines under ruthenium-catalyzed conditions has been developed. The acetyl group of N-acetyl-1,2-dihydroisoquinoline acts as a directing group for this C–H olefination strategy. Removal of the acetyl directing group by a simple method leads to a quick access to C-3 olefinated isoquinolines. The methodology is a very good alternative to the traditional Heck reaction and substrates with halogen substituents are very good candidates for the transformation.
Key words
ruthenium catalysis - C–H functionalization - isoquinolines - directing group - C–H olefinationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611807. Included are details of reversibility studies and kinetic isotope effect studies, spectra of new compounds, and crystal data of compound 3j.
- Supporting Information
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For some selected reviews on transition-metal-catalyzed C–H functionalization, see:
For two indirect methods, see: