4.6 Article

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

Journal

ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 23, Issue 8, Pages 1679-1685

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.9b00194

Keywords

NH-heteroarenes; quaternary ammonium salts; C-N cross-coupling; palladium catalysis; C-N bond cleavage

Funding

  1. National Natural Science Foundation of China [21372034]
  2. State Key Laboratory of Geohazard Prevention and Geoenvironment Protection [SICLGP2018Z002]

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In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)(2) and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.

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