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 |
|---|---|
| Pages (from-to) | 40-49 |
| Number of pages | 10 |
| Journal | Arkivoc |
| Volume | 2018 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 11 Oct 2017 |
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Keywords
- (Dichloroiodo)arenes
- Hypervalent iodine
- Iodopyridine
- Oxidation
- Recyclable reagents
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines : Recyclable hypervalent iodine reagents. / Yoshimura, Akira; Nguyen, Khiem C.; Nemykin, Victor N.; Zhdankin, Viktor V.
In: Arkivoc, Vol. 2018, No. 2, 11.10.2017, p. 40-49.Research output: Contribution to journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=85041114318&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85041114318&partnerID=8YFLogxK
U2 - 10.24820/ark.5550190.p010.279
DO - 10.24820/ark.5550190.p010.279
M3 - Article
AN - SCOPUS:85041114318
VL - 2018
SP - 40
EP - 49
JO - Arkivoc
JF - Arkivoc
SN - 1424-6376
IS - 2
ER -