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Iodine‐Catalyzed Decarboxylative Amidation of β,γ‐Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides
Author(s) -
Kiyokawa Kensuke,
Kojima Takumi,
Hishikawa Yusuke,
Minakata Satoshi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503298
Subject(s) - allylic rearrangement , chemistry , chloramine , catalysis , organic chemistry , iodine , amine gas treating , regioselectivity , decarboxylation , salt (chemistry) , amination , carboxylic acid , chlorine
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 I 2 , function as a key active species. The reaction provides an attractive alternative to existing methods for the synthesis of useful secondary allylic amine derivatives.