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Cyanoacetic Acid as a Masked Electrophile: Transition‐Metal‐Free Cyanomethylation of Amines and Carboxylic Acids
Author(s) -
Wang Hongxiang,
Shao Ying,
Zheng Hao,
Wang Hanghang,
Cheng Jiang,
Wan Xiaobing
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.201502733
Subject(s) - electrophile , carboxylic acid , chemistry , transition metal , cyanoacetic acid , organic chemistry , catalysis
Abstract Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α ‐aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination–decarboxylation of cyanoacetic acid in this transformation.