Literature DB >> 33570414

Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions.

Abigail J Shepard1,2, Julia A Townsend2, Christopher Foley1,2, Christopher Hulme1, Michael T Marty2, John C Jewett2.   

Abstract

Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.

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Year:  2021        PMID： 33570414      PMCID： PMC7955896          DOI： 10.1021/acs.orglett.1c00257

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions.

Authors:  Anna Roglans; Anna Pla-Quintana; Marcial Moreno-Mañas
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

2.  Water-soluble triazabutadienes that release diazonium species upon protonation under physiologically relevant conditions.

Authors:  Flora W Kimani; John C Jewett
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-06       Impact factor: 15.336

3.  Binuclear palladium(I) and palladium(II) complexes of ortho-functionalized 1,3-bis(aryl)triazenido ligands.

Authors:  Juan José Nuricumbo-Escobar; Carlos Campos-Alvarado; Gustavo Ríos-Moreno; David Morales-Morales; Patrick J Walsh; Miguel Parra-Hake
Journal:  Inorg Chem       Date:  2007-06-20       Impact factor: 5.165

4.  [45] Diazonium salts as specific reagents and probes of protein conformation.

Authors:  J F Riordan; B L Vallee
Journal:  Methods Enzymol       Date:  1972       Impact factor: 1.600

5.  Light-Activated Triazabutadienes for the Modification of a Viral Surface.

Authors:  Stephanie M Jensen; Flora W Kimani; John C Jewett
Journal:  Chembiochem       Date:  2016-10-21       Impact factor: 3.164

6.  Engineering Nanodisc Scaffold Proteins for Native Mass Spectrometry.

Authors:  Deseree J Reid; James E Keener; Andrew P Wheeler; Dane Evan Zambrano; Jessica M Diesing; Maria Reinhardt-Szyba; Alexander Makarov; Michael T Marty
Journal:  Anal Chem       Date:  2017-10-23       Impact factor: 6.986

7.  Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes.

Authors:  Can Liu; Zhiming Wang; Lei Wang; Pinhua Li; Yicheng Zhang
Journal:  Org Biomol Chem       Date:  2019-10-23       Impact factor: 3.876

8.  Cu-Click Compatible Triazabutadienes To Expand the Scope of Aryl Diazonium Ion Chemistry.

Authors:  Brandon M Cornali; Flora W Kimani; John C Jewett
Journal:  Org Lett       Date:  2016-09-13       Impact factor: 6.005

9.  Polymer-bound 1-aryl-3-alkyltriazenes as modular ligands for catalysis. Part 1: synthesis and metal coordination.

Authors:  Stefan Bräse; Stefan Dahmen; Frank Lauterwasser; Nicholas E Leadbeater; Emma L Sharp
Journal:  Bioorg Med Chem Lett       Date:  2002-07-22       Impact factor: 2.823

10.  Donor-acceptor triazenes: synthesis, characterization, and study of their electronic and thermal properties.

Authors:  Dimitri M Khramov; Christopher W Bielawski
Journal:  J Org Chem       Date:  2007-07-03       Impact factor: 4.354
  10 in total
  1 in total

1.  Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions.

Authors:  Garrett J Davis; Julia A Townsend; Madeline G Morrow; Mohamed Hamie; Abigail J Shepard; Chih-Chieh Hsieh; Michael T Marty; John C Jewett
Journal:  Bioconjug Chem       Date:  2021-11-03       Impact factor: 4.774
  1 in total

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