Expedient synthesis of long-chain ω-substituted fatty acids and esters from cyclic ketones using iodine and hydrogen peroxide

Research output: Contribution to journalArticle

Abstract

A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.

Original languageEnglish
Pages (from-to)4081-4088
Number of pages8
JournalSynthesis (Germany)
Volume50
Issue number20
DOIs
Publication statusPublished - 1 Jan 2018

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Ketones
Iodine
Carboxylic acids
Fatty acids
Hydrogen peroxide
Hydrogen Peroxide
Esters
Fatty Acids
Carboxylic Acids

Keywords

  • chelating reagents
  • cyclic ketones
  • di-(2-picolyl)amine
  • di-(2-pyridylmethylamino)alkanoic acids
  • ligands
  • ω-iodo-aliphatic carboxylic esters
  • ω-iodoaliphatic carboxylic acids

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Expedient synthesis of long-chain ω-substituted fatty acids and esters from cyclic ketones using iodine and hydrogen peroxide",
abstract = "A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.",
keywords = "chelating reagents, cyclic ketones, di-(2-picolyl)amine, di-(2-pyridylmethylamino)alkanoic acids, ligands, ω-iodo-aliphatic carboxylic esters, ω-iodoaliphatic carboxylic acids",
author = "Podrezova, {Ekaterina V.} and Larkina, {Maria S.} and Belousov, {Mikhail V.} and Andreas Kirschning and Zhdankin, {Viktor V.} and Yusubov, {Mekhman S.}",
year = "2018",
month = "1",
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doi = "10.1055/s-0036-1591598",
language = "English",
volume = "50",
pages = "4081--4088",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
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TY - JOUR

T1 - Expedient synthesis of long-chain ω-substituted fatty acids and esters from cyclic ketones using iodine and hydrogen peroxide

AU - Podrezova, Ekaterina V.

AU - Larkina, Maria S.

AU - Belousov, Mikhail V.

AU - Kirschning, Andreas

AU - Zhdankin, Viktor V.

AU - Yusubov, Mekhman S.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.

AB - A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.

KW - chelating reagents

KW - cyclic ketones

KW - di-(2-picolyl)amine

KW - di-(2-pyridylmethylamino)alkanoic acids

KW - ligands

KW - ω-iodo-aliphatic carboxylic esters

KW - ω-iodoaliphatic carboxylic acids

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U2 - 10.1055/s-0036-1591598

DO - 10.1055/s-0036-1591598

M3 - Article

VL - 50

SP - 4081

EP - 4088

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 20

ER -