title: Pharmaceutical-Oriented Selective Synthesis of Mononitriles and Dinitriles Directly from Methyl(hetero)arenes: Access to Chiral Nitriles and Citalopram.
abstract: A pharmaceutical-oriented, transition-metal-free, cyanide-free one-step direct transformation of methylarenes to aryl nitriles is described. For the dimethylarenes, the selectivity can be well-controlled to form mononitriles or dinitriles. Enantioenriched nitriles can also be synthesized by this method. As a pharmaceutically practical method, the antidepressant drug citalopram was synthesized from cheap and commercially abundant m-xylene on a gram scale in high yield, avoiding transition-metal residues and toxic cyanides.
authors.affiliation: Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.affiliation: Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Hong-Xing
authors.initials: HX
authors.lastname: Zheng
authors.affiliation: Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Chuan-Zhi
authors.initials: CZ
authors.lastname: Yao
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Bing-Feng
authors.initials: BF
authors.lastname: Sun
authors.affiliation: Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.
authors.forename: Yan-Biao
authors.initials: YB
authors.lastname: Kang
mesh_terms: D018687:Antidepressive Agents, Second-Generation / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D015283:Citalopram / Q000138:chemical synthesis*; D009570:Nitriles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014992:Xylenes / Q000737:chemistry*
chemical_list: D018687:Antidepressive Agents, Second-Generation; D009570:Nitriles; D014992:Xylenes; D015283:Citalopram