Literature DB >> 30109007

Efficient copper-catalyzed amination of DNA-conjugated aryl iodides under mild aqueous conditions.

Yves Ruff1, Frédéric Berst1.   

Abstract

Herein, we describe the development of copper-catalyzed cross-coupling of DNA-conjugated aryl iodides with aliphatic amines. This protocol leverages a novel ligand, 2-((2,6-dimethoxyphenyl)amino)-2-oxoacetic acid, to effect the transformation in aqueous DMSO, under mild conditions and in air, making it an ideal candidate for the synthesis of DNA-encoded libraries.

Entities:  

Year:  2018        PMID： 30109007      PMCID： PMC6072498          DOI： 10.1039/c8md00185e

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  28 in total

1.  Discovery of Potent and Selective Inhibitors for ADAMTS-4 through DNA-Encoded Library Technology (ELT).

Authors:  Yun Ding; Heather O'Keefe; Jennifer L DeLorey; David I Israel; Jeffrey A Messer; Cynthia H Chiu; Steven R Skinner; Rosalie E Matico; Monique F Murray-Thompson; Fan Li; Matthew A Clark; John W Cuozzo; Christopher Arico-Muendel; Barry A Morgan
Journal:  ACS Med Chem Lett       Date:  2015-07-07       Impact factor: 4.345

Review 2.  Chemical Biology Probes from Advanced DNA-encoded Libraries.

Authors:  Hazem Salamon; Mateja Klika Škopić; Kathrin Jung; Olivia Bugain; Andreas Brunschweiger
Journal:  ACS Chem Biol       Date:  2016-01-28       Impact factor: 5.100

3.  CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines.

Authors:  Wei Zhou; Mengyang Fan; Junli Yin; Yongwen Jiang; Dawei Ma
Journal:  J Am Chem Soc       Date:  2015-09-11       Impact factor: 15.419

4.  Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.

Authors:  Hui Zhang; Qian Cai; Dawei Ma
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

Review 5.  DNA-encoded chemistry: enabling the deeper sampling of chemical space.

Authors:  Robert A Goodnow; Christoph E Dumelin; Anthony D Keefe
Journal:  Nat Rev Drug Discov       Date:  2016-12-09       Impact factor: 84.694

6.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

7.  N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent.

Authors:  Yongbin Wang; Yu Zhang; Beibei Yang; Ao Zhang; Qizheng Yao
Journal:  Org Biomol Chem       Date:  2015-04-07       Impact factor: 3.876

8.  Efficient Buchwald-Hartwig-Migita Cross-Coupling for DNA Thioglycoconjugation.

Authors:  Nicolas Probst; Rémy Lartia; Océane Théry; Mouâd Alami; Eric Defrancq; Samir Messaoudi
Journal:  Chemistry       Date:  2018-01-16       Impact factor: 5.236

Review 9.  Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation.

Authors:  Subhajit Bhunia; Govind Goroba Pawar; S Vijay Kumar; Yongwen Jiang; Dawei Ma
Journal:  Angew Chem Int Ed Engl       Date:  2017-11-15       Impact factor: 15.336

Review 10.  Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development.

Authors:  Carlo Sambiagio; Stephen P Marsden; A John Blacker; Patrick C McGowan
Journal:  Chem Soc Rev       Date:  2014-03-03       Impact factor: 54.564
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  13 in total

1.  DNA-Compatible [3 + 2] Nitrone-Olefin Cycloaddition Suitable for DEL Syntheses.

Authors:  Christopher J Gerry; Zhenhua Yang; Michele Stasi; Stuart L Schreiber
Journal:  Org Lett       Date:  2019-02-14       Impact factor: 6.005

2.  DNA Barcoding a Complete Matrix of Stereoisomeric Small Molecules.

Authors:  Christopher J Gerry; Mathias J Wawer; Paul A Clemons; Stuart L Schreiber
Journal:  J Am Chem Soc       Date:  2019-06-25       Impact factor: 15.419

3.  Open-Air Alkylation Reactions in Photoredox-Catalyzed DNA-Encoded Library Synthesis.

Authors:  James P Phelan; Simon B Lang; Jaehoon Sim; Simon Berritt; Andrew J Peat; Katelyn Billings; Lijun Fan; Gary A Molander
Journal:  J Am Chem Soc       Date:  2019-02-12       Impact factor: 15.419

4.  Water-Compatible Cycloadditions of Oligonucleotide-Conjugated Strained Allenes for DNA-Encoded Library Synthesis.

Authors:  Matthias V Westphal; Liam Hudson; Jeremy W Mason; Johan A Pradeilles; Frédéric J Zécri; Karin Briner; Stuart L Schreiber
Journal:  J Am Chem Soc       Date:  2020-04-16       Impact factor: 15.419

Review 5.  DNA-Encoded Chemistry: Drug Discovery from a Few Good Reactions.

Authors:  Patrick R Fitzgerald; Brian M Paegel
Journal:  Chem Rev       Date:  2020-10-12       Impact factor: 72.087

6.  A Mild, DNA-Compatible Nitro Reduction Using B2(OH)4.

Authors:  Huang-Chi Du; Nicholas Simmons; John C Faver; Zhifeng Yu; Murugesan Palaniappan; Kevin Riehle; Martin M Matzuk
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

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

Authors:  Jian-Yuan Li; Gabriella Miklossy; Ram K Modukuri; Kurt M Bohren; Zhifeng Yu; Murugesan Palaniappan; John C Faver; Kevin Riehle; Martin M Matzuk; Nicholas Simmons
Journal:  Bioconjug Chem       Date:  2019-07-31       Impact factor: 4.774

8.  Homogeneous and Functional Group Tolerant Ring-Closing Metathesis for DNA-Encoded Chemical Libraries.

Authors:  Olivier B C Monty; Pranavanand Nyshadham; Kurt M Bohren; Murugesan Palaniappan; Martin M Matzuk; Damian W Young; Nicholas Simmons
Journal:  ACS Comb Sci       Date:  2020-01-21       Impact factor: 3.784

9.  Merging C(sp3)-H activation with DNA-encoding.

Authors:  Zhoulong Fan; Shuai Zhao; Tao Liu; Peng-Xiang Shen; Zi-Ning Cui; Zhe Zhuang; Qian Shao; Jason S Chen; Anokha S Ratnayake; Mark E Flanagan; Dominik K Kölmel; David W Piotrowski; Paul Richardson; Jin-Quan Yu
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

10.  C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis.

Authors:  Ying-Chu Chen; John C Faver; Angela F Ku; Gabriella Miklossy; Kevin Riehle; Kurt M Bohren; Melek N Ucisik; Martin M Matzuk; Zhifeng Yu; Nicholas Simmons
Journal:  Bioconjug Chem       Date:  2020-02-21       Impact factor: 4.774
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