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Cobalt‐Catalyzed C‐4 Selective Alkylation of Quinolines
Author(s) -
Yamamoto Shohei,
Saga Yutaka,
Andou Takashi,
Matsunaga Shigeki,
Kanai Motomu
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300991
Subject(s) - chemistry , alkylation , cobalt , selectivity , quinoline , pyridine , catalysis , yield (engineering) , medicinal chemistry , butyllithium , organic chemistry , combinatorial chemistry , materials science , metallurgy
The cobalt‐catalyzed direct C‐4 selective alkylation of quinolines is described. The reaction conditions used previously for pyridines were fully modified to achieve C‐4 selectivity in quinoline alkylation. Cobalt(II) acetate [Co(OAc) 2 ] (2–4 mol%) in combination with butyllithium (BuLi) and pyridine was best, and C‐4 alkylation proceeded in 54–95% yield with C‐4/C‐2=>20:1–2.5:1 and branched/linear=>20:1 selectivity.