Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents

Akira Yoshimura; Khiem C. Nguyen; Victor N. Nemykin; Viktor V. Zhdankin

doi:10.24820/ark.5550190.p010.279

Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents

Akira Yoshimura, Khiem C. Nguyen, Victor N. Nemykin, Viktor V. Zhdankin

Chemistry & Biochemistry

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

5 Scopus citations

Abstract

New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.

Original language	English (US)
Pages (from-to)	40-49
Number of pages	10
Journal	Arkivoc
Volume	2018
Issue number	2
DOIs	https://doi.org/10.24820/ark.5550190.p010.279
State	Published - Oct 11 2017

Bibliographical note

Funding Information:
This work was supported by a research grant from the NSF (CHE-1262479) and Tomsk Polytechnic University (VIU-316/2017).

Publisher Copyright:
© 2018 ARKAT USA, Inc.

Keywords

(Dichloroiodo)arenes
Hypervalent iodine
Iodopyridine
Oxidation
Recyclable reagents

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10.24820/ark.5550190.p010.279

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title = "Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents",

abstract = "New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.",

keywords = "(Dichloroiodo)arenes, Hypervalent iodine, Iodopyridine, Oxidation, Recyclable reagents",

author = "Akira Yoshimura and Nguyen, {Khiem C.} and Nemykin, {Victor N.} and Zhdankin, {Viktor V.}",

note = "Funding Information: This work was supported by a research grant from the NSF (CHE-1262479) and Tomsk Polytechnic University (VIU-316/2017). Publisher Copyright: {\textcopyright} 2018 ARKAT USA, Inc.",

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T1 - Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines

T2 - Recyclable hypervalent iodine reagents

AU - Yoshimura, Akira

AU - Nguyen, Khiem C.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor V.

PY - 2017/10/11

Y1 - 2017/10/11

N2 - New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.

AB - New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.

KW - (Dichloroiodo)arenes

KW - Hypervalent iodine

KW - Iodopyridine

KW - Oxidation

KW - Recyclable reagents

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JF - Arkivoc

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ER -

Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents

Abstract

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