Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids.
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.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123 (P.R. China).
Hongxiang
H
Wang
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123 (P.R. China). shaoying810724@163.com.|Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department, Changzhou University, Changzhou, 213164 (P.R. China). shaoying810724@163.com.
Ying
Y
Shao
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department, Changzhou University, Changzhou, 213164 (P.R. China).
Hao
H
Zheng
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123 (P.R. China).
Hanghang
H
Wang
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department, Changzhou University, Changzhou, 213164 (P.R. China).
Jiang
J
Cheng
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123 (P.R. China). wanxb@suda.edu.cn.
Xiaobing
X
Wan
cyanomethylation; decarboxylation; iodination; metal-free synthesis; nucleophilic substitution; α-aminonitriles