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

Ekaterina V. Podrezova; Maria S. Larkina; Mikhail V. Belousov; Andreas Kirschning; Viktor V. Zhdankin; Mekhman S. Yusubov

doi:10.1055/s-0036-1591598

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

Ekaterina V. Podrezova, Maria S. Larkina, Mikhail V. Belousov, Andreas Kirschning, Viktor V. Zhdankin, Mekhman S. Yusubov

Chemistry & Biochemistry

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

3 Scopus citations

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 language	English (US)
Pages (from-to)	4081-4088
Number of pages	8
Journal	Synthesis (Germany)
Volume	50
Issue number	20
DOIs	https://doi.org/10.1055/s-0036-1591598
State	Published - 2018

Keywords

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

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10.1055/s-0036-1591598

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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",

doi = "10.1055/s-0036-1591598",

language = "English (US)",

volume = "50",

pages = "4081--4088",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "20",

}

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

Y1 - 2018

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

UR - http://www.scopus.com/inward/record.url?scp=85054397855&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85054397855&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1591598

DO - 10.1055/s-0036-1591598

M3 - Article

AN - SCOPUS:85054397855

SN - 0039-7881

VL - 50

SP - 4081

EP - 4088

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 20

ER -

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

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