title: A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes.
abstract: A facile and general Brønsted acid-catalyzed deuteration at the methyl group of N-heteroarylmethanes was achieved through a dearomatic enamine intermediate under relatively mild reaction conditions. Both 2-methyl and 4-methyl groups in quinolines were deuterated with high deuterium incorporation. Pyridines, benzo[d]thiazoles, indoles and imines including these clinical drugs were also deuterated efficiently at the methyl groups. This reaction could be conducted on a large scale (500 mmol), showing its good potential for use in large-scale synthesis.
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. chentieqiao@hnu.edu.cn sf_yin@hnu.edu.cn.
authors.forename: Min
authors.initials: M
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. chentieqiao@hnu.edu.cn sf_yin@hnu.edu.cn.
authors.forename: Xue
authors.initials: X
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. chentieqiao@hnu.edu.cn sf_yin@hnu.edu.cn.
authors.forename: Tieqiao
authors.identifier: http://orcid.org/0000-0002-9787-9538
authors.initials: T
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. chentieqiao@hnu.edu.cn sf_yin@hnu.edu.cn.
authors.forename: Shuang-Feng
authors.identifier: http://orcid.org/0000-0003-2512-853X
authors.initials: SF
authors.lastname: Yin