Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 4, Pages 2234-2242Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03238
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Funding
- National Natural Science Foundation of China (NSFC) [21662024]
- Natural Science Foundation of Gansu Province [1606RJZA028]
- Foundation of A Hundred Youth Talents Training Program of Lanzhou Jiaotong University
- Young Scholars Science Foundation of Lanzhou Jiaotong University [2016008]
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alpha-Trichloromethylation of tertiary amines with trimethyl(trichloromethyl)silane by oxidative coupling, using DDQ as an oxidant, has been realized. The reaction is instantaneous, is scalable, and tolerates a broad range of functional groups and heteroarenes. The trichloromethylated products can be easily converted into beta,beta-dichloroamines, enamines, and alpha-amino acid esters under operationally simple conditions. This methodology provides an efficient alternative to the poisonous cyanation reactions for the synthesis of carboxylic acid and their derivatives.
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