Palladium-mediated Suzuki-Miyaura Cross-Coupling Reaction of Potassium Boc-protected aminomethyltrifluoroborate with DNA-Conjugated aryl bromides for DNA-Encoded chemical library synthesis

被引：17

作者：

Qu, Yi ^{[1
]}

Liu, Sixiu ^{[2
,3
]}

Wen, Huanan ^{[1
]}

Xu, Yanfen ^{[1
]}

An, Yulong ^{[1
]}

Li, Ke ^{[1
]}

Ni, Mengyuan ^{[1
]}

Shen, Yanfang ^{[1
]}

Shi, Xiaodong ^{[1
]}

Su, Wenji ^{[1
]}

Cui, Weiren ^{[1
]}

Kuai, Letian ^{[1
]}

Satz, Alexander L. ^{[1
]}

Yang, Hongfang ^{[1
]}

Lu, Xiaojie ^{[2
,3
]}

Peng, Xuanjia ^{[1
]}

机构：

[1] WuXi AppTec, DNA Encoded Lib Platform, 288 Fute Zhong Rd, Shanghai 200131, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhang Jiang Hitech Pk, Shanghai 201203, Peoples R China

[3] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China

来源：

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS | 2020年 / 533卷 / 02期

关键词：

DNA Encoded chemistry; Suzuki-miyaura cross-coupling; Potassium trifluoroborates; DESIGN; SELECTION; SYSTEM;

D O I：

10.1016/j.bbrc.2020.04.027

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A mild reaction for DNA-compatible, palladium promoted Suzuki-Miyaura cross-coupling reaction of potassium Boc-protected aminomethyltrifluoroborate with DNA-conjugated aryl bromides has been developed efficiently. This novel DNA encoded chemistry reaction proceeded well with a wide range of functional group tolerance, including aryl bromides and heteroaryl bromides. Further, the utility our DNA conjugated aminomethylated arene products is demonstrated by reaction with various types of reagents (including amide formation with carboxylic acids, alkylation with aldehydes, and carbamoylation with amines) as would be desired for the production of a DNA encoded library. (C) 2020 Elsevier Inc. All rights reserved.

引用

页码：209 / 214

页数：6

共 25 条

[1] Synthesis and Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides
Molander, Gary A.
Shin, Inji
ORGANIC LETTERS, 2011, 13 (15) : 3956 - 3959
[2] Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates
Molander, Gary A.
Shin, Inji
ORGANIC LETTERS, 2012, 14 (12) : 3138 - 3141
[3] Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborates
Shin, Inji d
Molander, Gary A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[4] Potassium Boc-Protected Secondary Aminomethyltrifluoroborates: Synthesis and Suzuki-Miyaura Cross-Coupling Reactions
Molander, Gary A.
Shin, Inji
ORGANIC LETTERS, 2012, 14 (17) : 4458 - 4461
[5] Palladium-Mediated Carbonylative Suzuki Coupling for DNA-Encoded Library Synthesis
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Simmons, Nicholas
Schuman, David P.
Shi, Zhicai
ORGANIC LETTERS, 2022, : 5214 - 5219
[6] C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis
Chen, Ying-Chu
Faver, John C.
Ku, Angela F.
Miklossy, Gabriella
Riehle, Kevin
Bohren, Kurt M.
Ucisik, Melek N.
Matzuk, Martin M.
Yu, Zhifeng
Simmons, Nicholas
BIOCONJUGATE CHEMISTRY, 2020, 31 (03) : 770 - 780
[7] Functional Group Tolerance of a Micellar on-DNA Suzuki-Miyaura Cross-Coupling Reaction for DNA-Encoded Library Design
Hunter, James H.
Potowski, Marco
Stanway-Gordon, Harriet A.
Madin, Andrew
Pairaudeau, Garry
Brunschweiger, Andreas
Waring, Michael J.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (24): : 17930 - 17935
[8] DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
Siripuram, Vijay Kumar
Sunkari, Yashoda Krishna
Nguyen, Thu-Lan
Flajolet, Marc
FRONTIERS IN CHEMISTRY, 2022, 10
[9] C-S Coupling of DNA-Conjugated Aryl Iodides for DNA-Encoded Chemical Library Synthesis
Ji, Yue
Dai, Dongliang
Luo, Huadong
Shen, Simin
Fan, Jing
Wang, Zhao
Chen, Min
Wan, Jinqiao
Li, Jin
Ma, Huiyong
Liu, Guansai
BIOCONJUGATE CHEMISTRY, 2021, 32 (04) : 685 - 689
[10] Mild and Efficient Palladium-Mediated C-N Cross-Coupling Reaction between DNA-Conjugated Aryl Bromides and Aromatic Amines
de Pedro Beato, Eduardo
Priego, Julian
Gironda-Martinez, Adrian
Gonzalez, Fernando
Benavides, Jesus
Blas, Jesus
Dolores Martin-Ortega, Maria
Angel Toledo, Miguel
Ezquerra, Jesus
Torrado, Alicia
ACS COMBINATORIAL SCIENCE, 2019, 21 (02) : 69 - 74

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