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Formation of Tertiary Alcohol via Chelation‐Assisted Nickel(II)‐Catalyzed Addition of Arylboronic Acids to Unactivated 1‐(Quinolin‐8‐yl)ethan‐1‐one
Author(s) -
Wu Shutao,
Guo Weijie,
Wang Tao,
Xie Qingxiao,
Wang Jianhui,
Liu Guiyan
Publication year - 2018
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.201800943
Subject(s) - chemistry , chelation , catalysis , nickel , alcohol , aryl , potassium carbonate , iodide , iodine , medicinal chemistry , tertiary alcohols , organic chemistry , alkyl
The synthesis of tertiary alcohol via chelation‐assisted nickel‐catalyzed addition of arylboronic acids to unactivated ketones was reported in this study. A series of substituted arylboronic acids was reacted with 1‐(quinolin‐8‐yl)ethan‐1‐one and its derivatives to provide various substituted 1‐aryl‐1‐(quinolin‐8‐yl)ethan‐1‐ols and relevant compounds in medium to good yields. The N‐directing group is essential for the addition reaction of arylboronic acids to these unactivated ketones. Nickel(II) acetylacetonate (10.0 mol%) in combination with sodium iodide (2 equiv.) and potassium carbonate (0.8 equiv.) was identified as the optimal catalytic system for the current transformations.