A practical, large-scale synthesis of pyrene-2-carboxylic acid

Juan M. Casas-Solvas; Tiddo J. Mooibroek; Shugantan Sandramurthy; Joshua D. Howgego; Anthony P Davis

doi:10.1055/s-0034-1379026

A practical, large-scale synthesis of pyrene-2-carboxylic acid

Juan M. Casas-Solvas
, Tiddo J. Mooibroek
, Shugantan Sandramurthy
, Joshua D. Howgego
, Anthony P Davis^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

12 Citations (Scopus)

Abstract

Pyrene-2-carboxylic acid is a versatile intermediate for introducing the unusual 2-pyrenyl unit into functional organic molecules. A classical preparation for this molecule has been revised and improved to give a robust and efficient three-step process. The method has been applied on a multigram scale to give pyrene-2-carboxylic acid in >70% overall yield from pyrene.

Original language	English
Article number	st-2014-d0576-l
Pages (from-to)	2591-2594
Number of pages	4
Journal	Synlett
Volume	25
Issue number	18
DOIs	https://doi.org/10.1055/s-0034-1379026
Publication status	Published - Nov 2014

Research Groups and Themes

Organic & Biological

Keywords

condensed aromatic compounds
electrophilic aromatic substitution
ring closure
ring opening
Haller-Bauer cleavage
2,7-FUNCTIONALIZED PYRENE DERIVATIVES
POLYCYCLIC AROMATIC-HYDROCARBONS
CARBON NANOTUBES
DNA MODIFICATION
NUCLEIC-ACIDS
HALLER-BAUER
PI-STACKING
CLEAVAGE
PROBES
BORYLATION

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10.1055/s-0034-1379026

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Cite this

@article{417fe7c81d7048e5b1f2a6157fa1ce6a,

title = "A practical, large-scale synthesis of pyrene-2-carboxylic acid",

abstract = "Pyrene-2-carboxylic acid is a versatile intermediate for introducing the unusual 2-pyrenyl unit into functional organic molecules. A classical preparation for this molecule has been revised and improved to give a robust and efficient three-step process. The method has been applied on a multigram scale to give pyrene-2-carboxylic acid in >70\% overall yield from pyrene.",

keywords = "condensed aromatic compounds, electrophilic aromatic substitution, ring closure, ring opening, Haller-Bauer cleavage, 2,7-FUNCTIONALIZED PYRENE DERIVATIVES, POLYCYCLIC AROMATIC-HYDROCARBONS, CARBON NANOTUBES, DNA MODIFICATION, NUCLEIC-ACIDS, HALLER-BAUER, PI-STACKING, CLEAVAGE, PROBES, BORYLATION",

author = "Casas-Solvas, \{Juan M.\} and Mooibroek, \{Tiddo J.\} and Shugantan Sandramurthy and Howgego, \{Joshua D.\} and Davis, \{Anthony P\}",

year = "2014",

month = nov,

doi = "10.1055/s-0034-1379026",

language = "English",

volume = "25",

pages = "2591--2594",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "18",

}

TY - JOUR

T1 - A practical, large-scale synthesis of pyrene-2-carboxylic acid

AU - Casas-Solvas, Juan M.

AU - Mooibroek, Tiddo J.

AU - Sandramurthy, Shugantan

AU - Howgego, Joshua D.

AU - Davis, Anthony P

PY - 2014/11

Y1 - 2014/11

N2 - Pyrene-2-carboxylic acid is a versatile intermediate for introducing the unusual 2-pyrenyl unit into functional organic molecules. A classical preparation for this molecule has been revised and improved to give a robust and efficient three-step process. The method has been applied on a multigram scale to give pyrene-2-carboxylic acid in >70% overall yield from pyrene.

AB - Pyrene-2-carboxylic acid is a versatile intermediate for introducing the unusual 2-pyrenyl unit into functional organic molecules. A classical preparation for this molecule has been revised and improved to give a robust and efficient three-step process. The method has been applied on a multigram scale to give pyrene-2-carboxylic acid in >70% overall yield from pyrene.

KW - condensed aromatic compounds

KW - electrophilic aromatic substitution

KW - ring closure

KW - ring opening

KW - Haller-Bauer cleavage

KW - 2,7-FUNCTIONALIZED PYRENE DERIVATIVES

KW - POLYCYCLIC AROMATIC-HYDROCARBONS

KW - CARBON NANOTUBES

KW - DNA MODIFICATION

KW - NUCLEIC-ACIDS

KW - HALLER-BAUER

KW - PI-STACKING

KW - CLEAVAGE

KW - PROBES

KW - BORYLATION

UR - https://www.scopus.com/pages/publications/84911898162

U2 - 10.1055/s-0034-1379026

DO - 10.1055/s-0034-1379026

M3 - Article (Academic Journal)

SN - 0936-5214

VL - 25

SP - 2591

EP - 2594

JO - Synlett

JF - Synlett

IS - 18

M1 - st-2014-d0576-l

ER -

A practical, large-scale synthesis of pyrene-2-carboxylic acid

Abstract

Research Groups and Themes

Keywords

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3-month Core Capability for Chemistry Research

From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.

Cite this

A practical, large-scale synthesis of pyrene-2-carboxylic acid

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

3-month Core Capability for Chemistry Research

From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.

Cite this