Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone

Qing Liu, Shuchen Yu, Liangzhen Hu, Muhamad Ijaz Hussain, Xiaohui Zhang, Yan Xiong

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.
Original languageEnglish (US)
Pages (from-to)7209-7217
Number of pages9
JournalTetrahedron
Volume74
Issue number50
DOIs
StatePublished - Dec 13 2018
Externally publishedYes

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