“One-Pot” Aminolysis/Thiol–Maleimide End-Group Functionalization of RAFT Polymers: Identifying and Preventing Michael Addition Side Reactions

2016 ◽  
Vol 49 (17) ◽  
pp. 6193-6202 ◽  
Author(s):  
Brooks A. Abel ◽  
Charles L. McCormick
Keyword(s):  
Michael Addition ◽  
Side Reactions ◽  
One Pot ◽  
End Group Functionalization ◽  
Raft Polymers ◽  
End Group

A Novel One-Pot Procedure for the Fast and Efficient Conversion of RAFT Polymers into Hydroxy-Functional Polymers

2009 ◽  
Vol 62 (8) ◽  
pp. 806 ◽  
Author(s):  
Till Gruendling ◽  
Mathias Dietrich ◽  
Christopher Barner-Kowollik
Keyword(s):  
Elevated Temperatures ◽  
Raft Polymerization ◽  
Functional Polymers ◽  
Size Exclusion ◽  
One Pot ◽  
Reversible Addition ◽  
Exclusion Chromatography ◽  
Azo Initiator ◽  
Raft Polymers ◽  
End Group

We report on the successful quantitative transformation of methacrylate and acrylate-type polymers prepared by reversible addition–fragmentation chain transfer (RAFT) polymerization carrying a dithioester-end-group into hydroxy-functional polymers. The simple reaction procedure involves stirring a solution of the dithioester-capped polymer and an azo-initiator in tetrahydrofuran at elevated temperatures (T = 60°C) in the presence of air. This reaction quantitatively yields hydroperoxide functionalities that can be efficiently reduced to hydroxy groups in a one-pot procedure using triphenylphosphine. Size exclusion chromatography–electrospray mass spectrometry was employed to monitor the progress of the reaction. The new backbone-linked hydroxy group provides a versatile anchor for chemical end-group conversions and conjugation reactions with prepared RAFT polymers, which alleviates problems with the rather limited ability of the dithioester-end-group to undergo non-radical transformations.

A straightforward approach for the one-pot synthesis of cyclic polymers from RAFT polymers via thiol–Michael addition

2016 ◽  
Vol 7 (9) ◽  
pp. 1782-1791 ◽  
Author(s):  
Junfei Zhao ◽  
Yanyan Zhou ◽  
Yu Zhou ◽  
Nianchen Zhou ◽  
Xiangqiang Pan ◽  
...  
Keyword(s):  
Michael Addition ◽  
One Pot ◽  
Cyclic Polymers ◽  
One Pot Synthesis ◽  
The One ◽  
Raft Polymers ◽  
Straightforward Approach

A straightforward approach for the synthesis of cyclic polymers in a one-pot reaction.

Versatile ω-end group functionalization of RAFT polymers using functional methane thiosulfonates

2009 ◽  
Vol 47 (12) ◽  
pp. 3118-3130 ◽  
Author(s):  
Peter J. Roth ◽  
Daniel Kessler ◽  
Rudolf Zentel ◽  
Patrick Theato
Keyword(s):  
End Group Functionalization ◽  
Raft Polymers ◽  
End Group

The first peripherally masked thiol dendrimers: a facile and highly efficient functionalization strategy of polyester dendrimers via one-pot xanthate deprotection/thiol–acrylate Michael addition reactions

2014 ◽  
Vol 50 (50) ◽  
pp. 6574-6577 ◽  
Author(s):  
Sam E. R. Auty ◽  
Oliver Andrén ◽  
Michael Malkoch ◽  
Steven P. Rannard
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
One Pot ◽  
Highly Efficient

We present the first xanthate surface functional dendrimers which undergo rapid one-pot deprotection to thiols and subsequent acrylate Michael addition .

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

One-Pot Synthesis of Highly Substituted Allenylidene Derivatives via Palladium- or Nickel-Catalyzed Tandem Michael Addition-Cyclization Reaction

2009 ◽  
Vol 351 (1-2) ◽  
pp. 141-146 ◽  
Author(s):  
Yun Shi ◽  
Jing Huang ◽  
Yan-Fang Yang ◽  
Lu-Yong Wu ◽  
Yan-Ning Niu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Cyclization Reaction ◽  
One Pot ◽  
One Pot Synthesis

Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

2021 ◽  
Author(s):  
Mohammad Bagher Teimouri ◽  
Zahra Mokhtare ◽  
Hamid Reza Khavasi
Keyword(s):  
Michael Addition ◽  
Heterocyclic Ring ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Chemical Bonds ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot

Three new chemical bonds and three stereogenic centres and one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

scholarly journals End group functionalization of poly(ethylene glycol) with phenolphthalein: towards star-shaped polymers based on supramolecular interactions

2014 ◽  
Vol 10 ◽  
pp. 2263-2269 ◽  
Author(s):  
Carolin Fleischmann ◽  
Hendrik Wöhlk ◽  
Helmut Ritter
Keyword(s):  
Ethylene Glycol ◽  
Cycloaddition Reaction ◽  
Supramolecular Interactions ◽  
Poly Ethylene Glycol ◽  
Naked Eye ◽  
Vis Spectroscopy ◽  
End Group Functionalization ◽  
Interesting Approach ◽  
Poly Ethylene ◽  
End Group

The synthesis of a new phenolphthalein azide derivative, which can be easily utilized in polymer analogous reactions, is presented. The subsequent cycloaddition reaction with propargyl-functionalized methoxypoly(ethylene glycol) yielded polymers bearing phenolphthalein as the covalently attached end group. In presence of per-β-cyclodextrin-dipentaerythritol, the formation of stable inclusion complexes was observed, representing an interesting approach towards the formation of star shaped polymers. The decolorization of a basic polymer solution caused by the complexation was of great advantage since this behavior enabled following the complex formation by UV–vis spectroscopy and even the naked eye.

ChemInform Abstract: One-Pot Three-Component Syntheses of Indoloquinolizidine Derivatives Using an Organocatalytic Michael Addition and Subsequent Pictet-Spengler Cyclization.

ChemInform ◽  
2012 ◽  
Vol 43 (7) ◽  
pp. no-no
Author(s):  
Xiaoyu Wu ◽  
Xiaoyang Dai ◽  
Huihui Fang ◽  
Linlin Nie ◽  
Jie Chen ◽  
...  
Keyword(s):  
Michael Addition ◽  
One Pot
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