Substrates as Electron-Donor Precursors: Synthesis of Naphtho-Fused Oxindoles via Benzannulation of 2-Halobenzaldehydes and Indolin-2-ones

作者：Jia, Feng-Cheng; Xu, Cheng; Zhou, Zhi-Wen; Cai, Qun; Wu, Yan-Dong^*; Wu, An-Xin^*

来源：Organic Letters, 2016, 18(20): 5232-5235.

DOI：10.1021/acs.orglett.6b02515

• AROMATIC 1,5-HYDROGEN TRANSFER
• C-H ARYLATION
• FREE-RADICAL REACTIONS
• UNACTIVATED ARENES
• ARYL HALIDES
• BIOLOGICAL-ACTIVITIES
• FISSISTIGMA-OLDHAMII
• PSCHORR CYCLIZATION
• COUPLING REACTIONS
• ALKALOIDS

An unusual benzannulation reaction has been realized by integrating intermolecular adol condensation with subsequent intramolercular base-promoted homolytic aromatic substitution. This novel cascade reaction provides a straightforward approach toward various naphtho-fused oxindoles from 2-halobenzaldehydes and indolin-2-ones in the presence of Cs2CO3 in DMSO. The enolates of indolin-2-ones as new and internal electron donors have been demonstrated to initiate intramolecular radical dehalogenative coupling.

• 出版日期2016-10-21
• 单位华中师范大学