Literature DB >> 29613783

Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization.

Emre H Discekici, Andre H St Amant, Shay N Nguyen, In-Hwan Lee1, Craig J Hawker, Javier Read de Alaniz.   

Abstract

The development and application of a novel endo furan-protected maleimide building block is reported. The endo isomer undergoes deprotection at temperatures ∼50 °C below the exo derivative. This enables a simple and powerful approach to quantitatively and selectively introduce functional maleimide groups via temperature modulation.

Entities:  

Year:  2018        PMID： 29613783      PMCID： PMC6205238          DOI： 10.1021/jacs.8b01544

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

Review 1.  Cu(0)-Mediated Living Radical Polymerization: A Versatile Tool for Materials Synthesis.

Authors:  Athina Anastasaki; Vasiliki Nikolaou; Gabit Nurumbetov; Paul Wilson; Kristian Kempe; John F Quinn; Thomas P Davis; Michael R Whittaker; David M Haddleton
Journal:  Chem Rev       Date:  2015-07-30       Impact factor: 60.622

2.  Additive-free clicking for polymer functionalization and coupling by tetrazine-norbornene chemistry.

Authors:  Claire F Hansell; Pieter Espeel; Milan M Stamenović; Ian A Barker; Andrew P Dove; Filip E Du Prez; Rachel K O'Reilly
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

3.  Light-Controlled Radical Polymerization: Mechanisms, Methods, and Applications.

Authors:  Mao Chen; Mingjiang Zhong; Jeremiah A Johnson
Journal:  Chem Rev       Date:  2016-03-15       Impact factor: 60.622

4.  Controlled Radical Polymerization as an Enabling Approach for the Next Generation of Protein-Polymer Conjugates.

Authors:  Emma M Pelegri-O'Day; Heather D Maynard
Journal:  Acc Chem Res       Date:  2016-09-02       Impact factor: 22.384

5.  Tetrazine-norbornene click reactions to functionalize degradable polymers derived from lactide.

Authors:  Ian A Barker; Daniel J Hall; Claire F Hansell; Filip E Du Prez; Rachel K O'Reilly; Andrew P Dove
Journal:  Macromol Rapid Commun       Date:  2011-09-01       Impact factor: 5.734

6.  Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts.

Authors:  Ryan M Pearson; Chern-Hooi Lim; Blaine G McCarthy; Charles B Musgrave; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2016-08-24       Impact factor: 15.419

7.  Design and synthesis of N-maleimido-functionalized hydrophilic polymers via copper-mediated living radical polymerization: a suitable alternative to PEGylation chemistry.

Authors:  Giuseppe Mantovani; François Lecolley; Lei Tao; David M Haddleton; Joost Clerx; Jeroen J L M Cornelissen; Kelly Velonia
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

8.  Organocatalyzed atom transfer radical polymerization driven by visible light.

Authors:  Jordan C Theriot; Chern-Hooi Lim; Haishen Yang; Matthew D Ryan; Charles B Musgrave; Garret M Miyake
Journal:  Science       Date:  2016-03-31       Impact factor: 47.728

9.  Synthesis of semitelechelic maleimide poly(PEGA) for protein conjugation by RAFT polymerization.

Authors:  Emmanuelle Bays; Lei Tao; Chien-Wen Chang; Heather D Maynard
Journal:  Biomacromolecules       Date:  2009-06-09       Impact factor: 6.988

Review 10.  The growing applications of click chemistry.

Authors:  John E Moses; Adam D Moorhouse
Journal:  Chem Soc Rev       Date:  2007-05-03       Impact factor: 54.564
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  8 in total

1.  Mapping the Morphological Landscape of Oligomeric Di-block Peptide-Polymer Amphiphiles.

Authors:  Benjamin P Allen; Zoe M Wright; Hailey F Taylor; Thomas J Oweida; Sabila Kader-Pinky; Emily F Patteson; Kara M Bucci; Caleb A Cox; Abishec Sundar Senthilvel; Yaroslava G Yingling; Abigail S Knight
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-27       Impact factor: 15.336

2.  Norbornadiene Chain-End Functional Polymers as Stable, Readily Available Precursors to Cyclopentadiene Derivatives.

Authors:  Sophia J Bailey; Emre H Discekici; Stephanie M Barbon; Shay N Nguyen; Craig J Hawker; Javier Read de Alaniz
Journal:  Macromolecules       Date:  2020-06-11       Impact factor: 5.985

3.  Norbornadienes: Robust and Scalable Building Blocks for Cascade "Click" Coupling of High Molecular Weight Polymers.

Authors:  Andre H St Amant; Emre H Discekici; Sophia J Bailey; Manuel S Zayas; Jung-Ah Song; Shelby L Shankel; Shay N Nguyen; Morgan W Bates; Athina Anastasaki; Craig J Hawker; Javier Read de Alaniz
Journal:  J Am Chem Soc       Date:  2019-08-19       Impact factor: 15.419

4.  Solvent Effects and Side Reactions in Organocatalyzed Atom Transfer Radical Polymerization for Enabling the Controlled Polymerization of Acrylates Catalyzed by Diaryl Dihydrophenazines.

Authors:  Blaine McCarthy; Steven Sartor; Justin Cole; Niels Damrauer; Garret M Miyake
Journal:  Macromolecules       Date:  2020-10-21       Impact factor: 5.985

5.  SLIM: A Short-Linked, Highly Redox-Stable Trityl Label for High-Sensitivity In-Cell EPR Distance Measurements.

Authors:  Nico Fleck; Caspar A Heubach; Tobias Hett; Florian R Haege; Pawel P Bawol; Helmut Baltruschat; Olav Schiemann
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-30       Impact factor: 15.336

6.  Photomediated core modification of organic photoredox catalysts in radical addition: mechanism and applications.

Authors:  Yajun Zhang; Dandan Jiang; Zheng Fang; Ning Zhu; Naixian Sun; Wei He; Chengkou Liu; Lili Zhao; Kai Guo
Journal:  Chem Sci       Date:  2021-06-10       Impact factor: 9.825

7.  Self-assembly using a retro Diels-Alder reaction.

Authors:  Jaeyoung Park; Jung-Moo Heo; Sicheon Seong; Jaegeun Noh; Jong-Man Kim
Journal:  Nat Commun       Date:  2021-07-09       Impact factor: 14.919

8.  Next-Generation Materials via Orthogonal Stimuli.

Authors:  Emre H Discekici; Javier Read de Alaniz
Journal:  ACS Cent Sci       Date:  2018-08-28       Impact factor: 14.553
  8 in total

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