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Synthesis 2015; 47(07): 976-984
DOI: 10.1055/s-0034-1380110
DOI: 10.1055/s-0034-1380110
paper
Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide
Further Information
Publication History
Received: 23 October 2014
Accepted after revision: 19 December 2014
Publication Date:
28 January 2015 (online)
Abstract
A new tandem catalytic process has been established for the synthesis of quinolines. This process utilizes the [IrCp*Cl2]2/KOH catalyzed isomerization/cyclization of allylic alcohols with 2-aminobenzyl alcohol. Both the secondary and primary allylic alcohols were investigated in this catalytic system to afford different substituted quinoline derivatives in moderate to good yields. A mechanism study showed the reaction following a tandem process integrating isomerization of allylic alcohols and oxidative cyclization of 2-aminobenzyl alcohol.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380110.
- Supporting Information
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For reviews, see:
For transition-metal-free indirect Friedländer quinoline synthesis, see:
{[IrCp*Cl2]2} was also used as an efficient catalyst for the hydrogen autotransfer (or hydrogen-borrowing) process, see: