title: Synthesis of 3-(aminomethyl)pyridine by traceless C3-selective umpolung of 1-amidopyridin-1-ium salts.
abstract: A natural product inspired rapid access of 3-(aminomethyl)pyridine by one-pot reaction of 1-amidopyridin-1-ium salt with aminal followed by reductive cleavage of the N-N bond is developed. This C3-selective formal C-H activation of pyridine features a traceless umpolung of the 1-amidopyridin-1-ium salt toward a Mannich type C-C bond formation of the in situ generated 1-amido-2-dialkylamino-1,2-dihydropyridine intermediate.
authors.affiliation: Key Lab of Synthetic Polymer of the Chinese Academy of Sciences, Green Chemistry and Process Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. wangbo@ciac.ac.cn dhxiao@ciac.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
authors.forename: Pingsheng
authors.initials: P
authors.lastname: Tang
authors.affiliation: Key Lab of Synthetic Polymer of the Chinese Academy of Sciences, Green Chemistry and Process Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. wangbo@ciac.ac.cn dhxiao@ciac.ac.cn.
authors.forename: Dehai
authors.initials: D
authors.lastname: Xiao
authors.affiliation: Key Lab of Synthetic Polymer of the Chinese Academy of Sciences, Green Chemistry and Process Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China. wangbo@ciac.ac.cn dhxiao@ciac.ac.cn.
authors.forename: Bo
authors.identifier: http://orcid.org/0000-0001-8104-1821
authors.initials: B
authors.lastname: Wang