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

[41] Development and Synthesis of DNA-Encoded Benzimidazole Library
Ding, Yun
Chai, Jing
Centrella, Paolo A.
Gondo, Chenaimwoyo
DeLorey, Jennifer L.
Clark, Matthew A.
ACS COMBINATORIAL SCIENCE, 2018, 20 (05) : 251 - 255
[42] Squaramide Formation for DNA-Encoded Library Synthesis
Douchez, Antoine
Poupart, Julien
Yang, Gaoqiang
Vaillancourt, Louis
Marinier, Anne
BIOCONJUGATE CHEMISTRY, 2024, 35 (07) : 963 - 970
[43] Design concepts for DNA-encoded library synthesis
Zhang, Y.
Clark, M. A.
BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 41
[44] Palladium-catalyzed coupling reaction of alkenylgalliums with aryl halides
Mikami, S
Yorimitsu, H
Oshima, K
SYNLETT, 2002, (07) : 1137 - 1139
[45] Recyclable Catalysts for Palladium-Catalyzed Aminations of Aryl Halides
Dumrath, Andreas
Luebbe, Christa
Neumann, Helfried
Jackstell, Ralf
Beller, Matthias
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (35) : 9599 - 9604
[46] A General Palladium-Catalyzed Amination of Aryl Halides with Ammonia
Schulz, Thomas
Torborg, Christian
Enthaler, Stephan
Schaeffner, Benjamin
Dumrath, Andreas
Spannenberg, Anke
Neumann, Helfried
Boerner, Armin
Beller, Matthias
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (18) : 4528 - 4533
[47] Mechanistic investigation of palladium-catalyzed amidation of aryl halides
Liang, Yun
Ren, Ying
Jia, Jianfeng
Wu, Hai-Shun
JOURNAL OF MOLECULAR MODELING, 2016, 22 (03) : 1 - 12
[48] Palladium-catalyzed homocouplingr of aryl halides in the presence of fluoride
Seganish, WM
Mowery, ME
Riggleman, S
DeShong, P
TETRAHEDRON, 2005, 61 (08) : 2117 - 2121
[49] PALLADIUM-CATALYZED FORMYLATION OF ARYL, HETEROCYCLIC, AND VINYLIC HALIDES
SCHOENBERG, A
HECK, RF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) : 7761 - 7764
[50] Palladium-catalyzed cyclocotrimerization of propargyl alcohols with aryl halides
Oi, S
Orihara, H
Kawai, H
Inoue, Y
HETEROCYCLES, 2005, 66 : 621 - 625

← 1 2 3 4 5 →