Organic Synthesis on Soluble Polymer Supports:  Liquid-Phase Methodologies

Organocatalysts have been extensively studied for the past few decades as alternatives to transition-metal catalysts. Immobilizing organocatalysts on polymer supports allows easy recovery and simple product purification after a reaction. Select examples of recent reports that describe the potential advantages of using soluble polymers to prepare soluble polymer-supported organocatalysts useful in organic synthesis are reviewed.

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Universal Soluble Polymer Supports with Precisely Controlled Loading Capacity for Sequence‐Defined Oligomer Synthesis

Journal of Polymer Science Part A Polymer Chemistry ◽

10.1002/pola.29218 ◽

2018 ◽

Vol 57 (3) ◽

pp. 403-410 ◽

Cited By ~ 1

Author(s):

Laurence Oswald ◽

Abdelaziz Al Ouahabi ◽

Chloé Laure ◽

Jean‐Arthur Amalian ◽

Laurence Charles ◽

...

Keyword(s):

Loading Capacity ◽

Soluble Polymer ◽

Polymer Supports ◽

Soluble Polymer Supports

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Molecular Transporter Between Polymer Platforms: Highly Efficient Chemoenzymatic Glycopeptide Synthesis by the Combined Use of Solid-Phase and Water-Soluble Polymer Supports

Angewandte Chemie International Edition ◽

10.1002/anie.200463065 ◽

2005 ◽

Vol 44 (17) ◽

pp. 2534-2537 ◽

Cited By ~ 32

Author(s):

Masataka Fumoto ◽

Hiroshi Hinou ◽

Takahiko Matsushita ◽

Masaki Kurogochi ◽

Takashi Ohta ◽

...

Keyword(s):

Solid Phase ◽

Water Soluble ◽

Soluble Polymer ◽

Water Soluble Polymer ◽

Highly Efficient ◽

Polymer Supports ◽

Combined Use ◽

Soluble Polymer Supports

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Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis

Chemical Reviews ◽

10.1021/cr8004235 ◽

2009 ◽

Vol 109 (2) ◽

pp. 530-582 ◽

Cited By ~ 278

Author(s):

David E. Bergbreiter ◽

Jianhua Tian ◽

Chayanant Hongfa

Keyword(s):

Homogeneous Catalysis ◽

Soluble Polymer ◽

Polymer Supports ◽

Soluble Polymer Supports

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Soluble polymer supports for homogeneous catalysis in flow reactions

Pure and Applied Chemistry ◽

10.1515/pac-2016-0801 ◽

2016 ◽

Vol 88 (10-11) ◽

pp. 953-960 ◽

Cited By ~ 2

Author(s):

Yannan Liang ◽

Christopher Watson ◽

Thomas Malinski ◽

Justin Tepera ◽

David E. Bergbreiter

Keyword(s):

Transition Metal ◽

Homogeneous Catalysis ◽

Flow Chemistry ◽

Ring Closing Metathesis ◽

Soluble Polymer ◽

Liquid Separation ◽

Nucleophilic Catalysis ◽

Substrate Solution ◽

Polymer Supports ◽

Soluble Polymer Supports

AbstractThe use of polyisobutylene and poly(4-dodecylstyrene) bound catalysts that contain transition metal or organocatalysts for cyclopropanation, ring-closing metathesis, and nucleophilic catalysis in flow chemistry schemes is described and compared with similar catalysts used in batch reactions. These Rh(II) carboxylate catalysts, N-heterocyclic carbene-ligated Ru(II) benzylidene catalysts, and analogs of 4-dimethylaminopyridine catalysts were used in reactions in heptane in flow and then separated in a gravity based liquid/liquid separation using a biphasic heptane/acetonitrile mixture. The less dense catalyst-containing phase in that separation was continuously used in flow with fresh substrate solution. Leaching of catalysts, yields, and turnover frequencies in these flow reactions were comparable with prior results obtained with the same phase isolable catalysts in batch reactions.

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Synthesis of oligoarylacetylenes with defined conjugated sequences using tailor-made soluble polymer supports

Chemical Communications ◽

10.1039/c7cc03633g ◽

2017 ◽

Vol 53 (59) ◽

pp. 8312-8315 ◽

Cited By ~ 9

Author(s):

Roza Szweda ◽

Christophe Chendo ◽

Laurence Charles ◽

Paul N. W. Baxter ◽

Jean-François Lutz

Keyword(s):

Synthesis And Characterization ◽

Soluble Polymer ◽

Polymer Supports ◽

Soluble Polymer Supports

The use of polystyrene-based soluble polymer supports greatly simplifies the synthesis and characterization of self-aggregating sequence-defined oligoarylacetylenes.

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