Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide

Shu-jie Chen; Guo-ping Lu; Chun Cai

doi:10.1055/s-0034-1380110

Synthesis, Table of Contents

Synthesis 2015; 47(07): 976-984
DOI: 10.1055/s-0034-1380110

paper

Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide

Shu-jie Chen

Chemical Engineering College, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing, Jiangsu 210094, P. R. of China Email: c.cai@mail.njust.edu.cn

,

Guo-ping Lu

Chemical Engineering College, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing, Jiangsu 210094, P. R. of China Email: c.cai@mail.njust.edu.cn

,

Chun Cai*

Chemical Engineering College, Nanjing University of Science & Technology, 200 Xiaolingwei, Nanjing, Jiangsu 210094, P. R. of China Email: c.cai@mail.njust.edu.cn

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Abstract

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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.

Key words

iridium - quinolines - allylic alcohol - isomerization - cyclization

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References

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