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Reductive C2‐Alkylation of Pyridine and Quinoline N ‐Oxides Using Wittig Reagents
Author(s) -
Han Sangil,
Chakrasali Prashant,
Park Jihye,
Oh Hyunjung,
Kim Saegun,
Kim Kyuneun,
Pandey Ashok Kumar,
Han Sang Hoon,
Han Soo Bong,
Kim In Su
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807159
Subject(s) - quinoline , alkylation , pyridine , chemistry , reagent , wittig reaction , combinatorial chemistry , selectivity , organic chemistry , catalysis
The ability to alkylate pyridines and quinolines is important for their further development as pharmaceuticals and agrochemicals, and for other purposes. Herein we describe the unprecedented reductive alkylation of pyridine and quinoline N ‐oxides using Wittig reagents. A wide range of pyridine and quinoline N ‐oxides were converted into C2‐alkylated pyridines and quinolines with excellent site selectivity and functional‐group compatibility. Sequential C−H functionalization reactions of pyridine and quinoline N ‐oxides highlight the utility of the developed method. Detailed labeling experiments were performed to elucidate the mechanism of this process.