2023
DOI: 10.1002/adsc.202300661
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Iron‐Catalyzed Transfer Hydrogenation: Divergent Synthesis of Quinolines and Quinolones from ortho‐Nitrobenzyl Alcohols

Simin Chun,
Ramachandra Reddy Putta,
Junhwa Hong
et al.

Abstract: Herein, we report the divergent synthesis of quinolines and quinolones via a transfer hydrogenative condensation of ortho‐nitrobenzyl alcohols in one step. The reaction proceeded using the cyclopentadienone iron complex without any additional redox reagents. After transfer hydrogenation between ortho‐nitrobenzyl alcohols and secondary alcohols, the subsequent Friedländer annulation affords polysubstituted quinoline products in 22‐90% (39 examples). The developed method was also applied to synthesize quinolones… Show more

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Cited by 6 publications
(3 citation statements)
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“…33 More recently, Chun et al have shown that a cyclopentadienone iron complex can be employed for the synthesis of quinolines and quinolones through transfer hydrogenative condensation of ortho-nitrobenzyl alcohols in the presence of trimethylamine oxide (TMAO). 34 It is important to emphasize that these methodologies, though effective, require harsh reaction conditions such as high temperature (120−160 °C), longer reaction times (18−48 h), and large catalyst loading (1.5−5 mol %), resulting in moderate yields of quinolines (Table S1). Besides, the need for extra additives limits the substrate scope, while the use of airand moisture-sensitive toxic phosphine ligands remains a challenge for further developments in this field.…”
Section: ■ Introductionmentioning
confidence: 99%
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“…33 More recently, Chun et al have shown that a cyclopentadienone iron complex can be employed for the synthesis of quinolines and quinolones through transfer hydrogenative condensation of ortho-nitrobenzyl alcohols in the presence of trimethylamine oxide (TMAO). 34 It is important to emphasize that these methodologies, though effective, require harsh reaction conditions such as high temperature (120−160 °C), longer reaction times (18−48 h), and large catalyst loading (1.5−5 mol %), resulting in moderate yields of quinolines (Table S1). Besides, the need for extra additives limits the substrate scope, while the use of airand moisture-sensitive toxic phosphine ligands remains a challenge for further developments in this field.…”
Section: ■ Introductionmentioning
confidence: 99%
“…The direct synthesis of quinolines from 2-nitrobenzyl alcohol and secondary alcohols is currently limited to only four reports (Scheme ). While one of these systems reported by Maji et al employs an expensive iridium cyclopentadienyl complex, the other three reports deal with iron-based catalytic systems. For example, Xie et al showcased quinoline synthesis from 2-nitroaryl alcohol by employing Ru 3 (CO) 12 with expensive 1,1′-bis­(diphenyl phosphino)­ferrocene (dppf) in the presence of potassium tert-butoxide as the catalytic system .…”
Section: Introductionmentioning
confidence: 99%
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