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Transition‐Metal‐Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
Author(s) -
Jin Hao,
Chen Xinzhi,
Qian Chao,
Ge Xin,
Zhou Shaodong
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100588
Subject(s) - chemistry , amide , alkyl , sulfur , transition metal , aryl , halide , alkane , amine gas treating , functional group , organic chemistry , combinatorial chemistry , catalysis , polymer
A general method for one‐pot synthesis of thioamides is developed through a three‐component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C−N coupling by‐product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.