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Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides.
Chemistry. 2015 Oct 26; 21(44):15548-52.C

Abstract

The iodine-catalyzed decarboxylative amidation of β,γ-unsaturated carboxylic acids with chloramine salts is described. This method enables the regioselective synthesis of allylic amides from various types of β,γ-unsaturated carboxylic acids containing substituents at the α- and β-positions. In the reaction, N-iodo-N-chloroamides, generated by the reaction of a chloramine salt with I2 , function as a key active species. The reaction provides an attractive alternative to existing methods for the synthesis of useful secondary allylic amine derivatives.

Authors+Show Affiliations

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan).Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan).Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan).Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan). minakata@chem.eng.osaka-u.ac.jp.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

26493878

Citation

Kiyokawa, Kensuke, et al. "Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids With Chloramine Salts Leading to Allylic Amides." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 21, no. 44, 2015, pp. 15548-52.
Kiyokawa K, Kojima T, Hishikawa Y, et al. Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides. Chemistry. 2015;21(44):15548-52.
Kiyokawa, K., Kojima, T., Hishikawa, Y., & Minakata, S. (2015). Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides. Chemistry (Weinheim an Der Bergstrasse, Germany), 21(44), 15548-52. https://doi.org/10.1002/chem.201503298
Kiyokawa K, et al. Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids With Chloramine Salts Leading to Allylic Amides. Chemistry. 2015 Oct 26;21(44):15548-52. PubMed PMID: 26493878.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides. AU - Kiyokawa,Kensuke, AU - Kojima,Takumi, AU - Hishikawa,Yusuke, AU - Minakata,Satoshi, Y1 - 2015/09/10/ PY - 2015/08/20/received PY - 2015/10/24/entrez PY - 2015/10/24/pubmed PY - 2015/10/24/medline KW - amidation KW - amines KW - chloramine salt KW - decarboxylation KW - iodine SP - 15548 EP - 52 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 44 N2 - The iodine-catalyzed decarboxylative amidation of β,γ-unsaturated carboxylic acids with chloramine salts is described. This method enables the regioselective synthesis of allylic amides from various types of β,γ-unsaturated carboxylic acids containing substituents at the α- and β-positions. In the reaction, N-iodo-N-chloroamides, generated by the reaction of a chloramine salt with I2 , function as a key active species. The reaction provides an attractive alternative to existing methods for the synthesis of useful secondary allylic amine derivatives. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/26493878/Iodine_Catalyzed_Decarboxylative_Amidation_of_βγ_Unsaturated_Carboxylic_Acids_with_Chloramine_Salts_Leading_to_Allylic_Amides_ L2 - https://doi.org/10.1002/chem.201503298 DB - PRIME DP - Unbound Medicine ER -
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