Transition-Metal-Free Base-Controlled C−N Coupling Reactions: Selective Mono Versus Diarylation of Primary Amines with 2-Chlorobenzimidazoles

Wei Sang, Yan Yan Gong, Hua Cheng, Rui Zhang, Ye Yuan, Guang Gao Fan, Zhi Qin Wang, Cheng Chen, Francis Verpoort

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, a base-controlled protocol was developed for the C−N coupling of primary amines and 2-chlorobenzimidazoles, affording a handful of secondary or tertiary amines in a selective fashion. Moreover, this protocol was realized under transition-metal-free conditions, and the variation of the base from iPr2NH to LiOtBu completely switched the selectivity from monoarylation to diarylation. Further investigations elucidated that the variety, intrinsic basicity and amount of the utilized bases considerably affected these reactions. (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • 2-aminobenzimidazoles
  • base-controlled
  • C−N coupling
  • diarylation
  • monoarylation
  • transition-metal-free

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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