1. Acid-catalyzed regioselective remote heteroarylation of alkenes via C=C bond migration.
- Author
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Qin, Shengxiang, Zhang, Yaqi, Jiang, Long, Tse, Man Kin, Chan, Albert S. C., and Qiu, Liqin
- Subjects
COPPER ,FUNCTIONAL groups ,ALKENES ,ALKANES - Abstract
We report herein the acid-catalyzed regioselective remote heteroarylation and reductive alkylation of alkenes. Various alkenes, including mono-, di-, and tri-substituted alkenes and cyclic alkenes, are applicable to this reaction. This method exhibits broad substrate scope, high functional group tolerance and high atomic economy. In addition, both gram-scale synthesis and product transformations demonstrate the potential utility of this reaction. It also provides an efficient and novel pathway to establish the valuable framework of 1,1-diaryl alkanes. Further mechanistic studies suggested that TfOH in situ generated by Cu(OTf)
2 and trace H2 O catalyzed the alkene migration. Then, heteroarylation was conducted by Friedel–Crafts type alkylation. [ABSTRACT FROM AUTHOR]- Published
- 2024
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