PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Eric Valeur; Mark Bradley

doi:10.1016/j.tet.2007.06.019

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Eric Valeur, Mark Bradley

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

Abstract

Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8855-8871
Number of pages	17
Journal	Tetrahedron
Volume	63
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2007.06.019
Publication status	Published - 3 Sept 2007

Keywords / Materials (for Non-textual outputs)

PEPTIDE-SYNTHESIS
CONVENIENT REAGENT
ORGANIC-SYNTHESIS
AMINO-ACIDS
DERIVATIVES
COMPLEXES
BOP

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10.1016/j.tet.2007.06.019

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title = "PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation",

abstract = "Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "PEPTIDE-SYNTHESIS, CONVENIENT REAGENT, ORGANIC-SYNTHESIS, AMINO-ACIDS, DERIVATIVES, COMPLEXES, BOP",

author = "Eric Valeur and Mark Bradley",

year = "2007",

month = sep,

day = "3",

doi = "10.1016/j.tet.2007.06.019",

language = "English",

volume = "63",

pages = "8855--8871",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "36",

}

TY - JOUR

T1 - PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

AU - Valeur, Eric

AU - Bradley, Mark

PY - 2007/9/3

Y1 - 2007/9/3

N2 - Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%. (c) 2007 Elsevier Ltd. All rights reserved.

AB - Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%. (c) 2007 Elsevier Ltd. All rights reserved.

KW - PEPTIDE-SYNTHESIS

KW - CONVENIENT REAGENT

KW - ORGANIC-SYNTHESIS

KW - AMINO-ACIDS

KW - DERIVATIVES

KW - COMPLEXES

KW - BOP

U2 - 10.1016/j.tet.2007.06.019

DO - 10.1016/j.tet.2007.06.019

M3 - Article

SN - 0040-4020

VL - 63

SP - 8855

EP - 8871

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Abstract

Keywords / Materials (for Non-textual outputs)

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