Formation of Tertiary Alcohol via Chelation-Assisted Nickel(II)-Catalyzed Addition of Arylboronic Acids to Unactivated 1-(Quinolin-8-yl)ethan-1-one

被引：5

作者：

Wu, Shutao ^{[1
]}

Guo, Weijie ^{[2
]}

Wang, Tao ^{[1
]}

Xie, Qingxiao ^{[1
]}

Wang, Jianhui ^{[1
]}

Liu, Guiyan ^{[2
]}

机构：

[1] Tianjin Univ, Dept Chem, Coll Sci, Tianjin 300350, Peoples R China

[2] Tianjin Normal Univ, Tianjin Key Lab Struct & Performance Funct Mol, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Coll Chem, Tianjin 300387, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Tertiary alcohol; Chelation-assisted; Arylboronic acids; Unactivated ketones; Addition reaction; RHODIUM-CATALYZED ADDITION; ZEROVALENT PALLADIUM COMPLEXES; ARYL BORONIC ACIDS; OXIDATIVE ADDITION; ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE FORMATION; ASYMMETRIC ADDITION; CONJUGATE ADDITION; ALPHA-KETOESTERS; HALIDE-IONS;

D O I：

10.1002/adsc.201800943

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：4533 / 4542

页数：10

共 2 条

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Zhu, Wen-Jing
Yu, Xiao
Liu, Hong-Yan
Liu, Yi
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Zhang, Peng-Fei
Xia, Cheng-Cai
Li, Fu-Rong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (31) : 6307 - 6311
[2] Crystal structure of bis(acetato-κO)-bis(1-(pyridin2-yl)ethan-1-one oxime-κ2N,N') nickel(II), C18H22N4NiO6
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ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2018, 233 (02): : 329 - 330

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