Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis

被引：27

作者：

Li, Jian-Yuan ^{[1
]}

Miklossy, Gabriella ^{[1
]}

Modukuri, Ram K. ^{[1
]}

Bohren, Kurt M. ^{[1
]}

Yu, Zhifeng ^{[1
]}

Palaniappan, Murugesan ^{[1
]}

Faver, John C. ^{[1
]}

Riehle, Kevin ^{[1
]}

Matzuk, Martin M. ^{[1
]}

Simmons, Nicholas ^{[1
]}

机构：

[1] Baylor Coll Med, Ctr Drug Discovery, Dept Pathol & Immunol, Houston, TX 77030 USA

来源：

BIOCONJUGATE CHEMISTRY | 2019年 / .30卷 / 08期

基金：

美国国家卫生研究院;

关键词：

SOLUBLE EPOXIDE HYDROLASE; COUPLING REACTIONS; SELECTION METHODS; SUZUKI-MIYAURA; ARYL HALIDES; INHIBITORS; OPTIMIZATION; EFFICIENT; LIGANDS; SYSTEM;

D O I：

10.1021/acs.bioconjchem.9b00447

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chemical conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chemical library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

引用

页码：2209 / 2215

页数：7

共 50 条

[31] Palladium-catalyzed decarboxylative vinyltrifluoromethylation of aryl halides
Suppan, Kathiravan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[32] Progress in palladium-catalyzed amination of aryl halides
Liu, P
Li, SH
Li, LM
Wang, XR
Yin, YQ
Zhang, YH
PROGRESS IN CHEMISTRY, 2005, 17 (02) : 286 - 292
[33] The synthesis of triarylamine macromolecules by palladium-catalyzed amination of aryl halides.
Hartwig, JF
Gooson, FE
Louie, J
Hauck, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U413 - U413
[34] Synthesis of Dienes by Palladium-Catalyzed Couplings of Tosylhydrazones with Aryl and Alkenyl Halides
Barluenga, Jose
Tomas-Gamasa, Maria
Aznar, Fernando
Valdes, Carlos
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3235 - 3240
[35] Synthesis of dialkyl cyanoboronates and their application in palladium-catalyzed cyanation of aryl halides
Jiang, B
Kan, Y
Zhang, A
TETRAHEDRON, 2001, 57 (08) : 1581 - 1584
[36] Ligand-Free Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides under Ambient Conditions: Synthesis of Aromatic Carboxylic Acids and Aromatic Esters
Han, Wei
Jin, Fengli
Zhou, Qing
SYNTHESIS-STUTTGART, 2015, 47 (13): : 1861 - 1868
[37] Palladium-Mediated Carbonylative Suzuki Coupling for DNA-Encoded Library Synthesis
Chheda, Pratik R.
Simmons, Nicholas
Schuman, David P.
Shi, Zhicai
ORGANIC LETTERS, 2022, : 5214 - 5219
[38] Environmentally Benign Carbonylation Reaction: Palladium-Catalyzed Hydroxycarbonylation of Aryl Halides and Benzyl Chloride Derivatives in Ionic Liquid Media
Eiichiro Mizushima
Teruyuki Hayashi
Masato Tanaka
Topics in Catalysis, 2004, 29 : 163 - 166
[39] Environmentally benign carbonylation reaction: palladium-catalyzed hydroxycarbonylation of aryl halides and benzyl chloride derivatives in Ionic liquid media
Mizushima, E
Hayashi, T
Tanaka, M
TOPICS IN CATALYSIS, 2004, 29 (3-4) : 163 - 166
[40] Palladium-catalyzed prenylation of (hetero)aryl boronic acids
Leister, Jeffrey
Chao, Darrian
Billingsley, Kelvin L.
TETRAHEDRON LETTERS, 2021, 66

← 1 2 3 4 5 →