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Cyanoacetic Acid as a Masked Electrophile: Transition‐Metal‐Free Cyanomethylation of Amines and Carboxylic Acids
Authors:Hongxiang Wang  Prof. Dr. Ying Shao  Hao Zheng  Hanghang Wang  Prof. Dr. Jiang Cheng  Prof. Dr. Xiaobing Wan
Affiliation:1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123 (P.R. China);2. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department, Changzhou University, Changzhou, 213164 (P.R. China)
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.
Keywords:α  ‐aminonitriles  cyanomethylation  decarboxylation  iodination  metal‐free synthesis  nucleophilic substitution
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