One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

Sagi Eppel; Moshe Portnoy

doi:10.1016/j.tetlet.2013.07.034

One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

Sagi Eppel, Moshe Portnoy

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin.

Original language	English
Pages (from-to)	5056-5060
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2013.07.034
State	Published - 11 Sep 2013
Externally published	Yes

Keywords

Click chemistry
Eglinton coupling
Esterification
Glaser coupling
One-pot reactions
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.07.034

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title = "One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin",

abstract = "We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin.",

keywords = "Click chemistry, Eglinton coupling, Esterification, Glaser coupling, One-pot reactions, Solid-phase synthesis",

author = "Sagi Eppel and Moshe Portnoy",

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doi = "10.1016/j.tetlet.2013.07.034",

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T1 - One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

AU - Eppel, Sagi

AU - Portnoy, Moshe

PY - 2013/9/11

Y1 - 2013/9/11

N2 - We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin.

AB - We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin.

KW - Click chemistry

KW - Eglinton coupling

KW - Esterification

KW - Glaser coupling

KW - One-pot reactions

KW - Solid-phase synthesis

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U2 - 10.1016/j.tetlet.2013.07.034

DO - 10.1016/j.tetlet.2013.07.034

M3 - Article

AN - SCOPUS:84881139448

SN - 0040-4039

VL - 54

SP - 5056

EP - 5060

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

One-pot esterification-click (CuAAC) and esterification-acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

Abstract

Keywords

ASJC Scopus subject areas

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