Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones

被引：50

作者：

Kim, Donghee ^{[1
]}

Ham, Kyungrok ^{[1
]}

Hong, Sungwoo ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 36期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC 1,4-ADDITION; ALPHA; BETA-UNSATURATED KETONES; ACETYLENES; ANNULATION; ALDEHYDES; CHALCONE; CATALYST; IODIDES;

D O I：

10.1039/c2ob26061a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The remarkable catalytic effects of Fe(OTf)(3) in the context of the Pd(II)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

引用

页码：7305 / 7312

页数：8

共 25 条

[21] Indole Synthesis by Conjugate Addition of Anilines to Activated Acetylenes and an Unusual Ligand-Free Copper(II)-Mediated Intramolecular Cross-Coupling [J].

Gao, Detian ;

Back, Thomas G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (46) :14828-14840

[22] Ligand-Free Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides under Ambient Conditions: Synthesis of Aromatic Carboxylic Acids and Aromatic Esters [J].

Han, Wei ;

Jin, Fengli ;

Zhou, Qing .

SYNTHESIS-STUTTGART, 2015, 47 (13) :1861-1868

[23] Ligand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions [J].

Walker, Sarah E. ;

Boehnke, Julian ;

Glen, Pauline E. ;

Levey, Steven ;

Patrick, Lisa ;

Jordan-Hore, James A. ;

Lee, Ai-Lan .

ORGANIC LETTERS, 2013, 15 (08) :1886-1889

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

Wu, Shutao ;

Guo, Weijie ;

Wang, Tao ;

Xie, Qingxiao ;

Wang, Jianhui ;

Liu, Guiyan .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) :4533-4542

[25] Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters [J].

Kikushima, Kotaro ;

Holder, Jeffrey C. ;

Gatti, Michele ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :6902-6905

← 1 2 3 →