Sonogashira Cross-Coupling of Aryl Ammonium Salts by Selective C-N Activation Catalyzed by Air- and Moisture-Stable, Highly Active [Pd(NHC)(3-CF₃-An)Cl₂] (An = Aniline) Precatalysts

Peng Lei*, Yibo Wang, Caixia Zhang, Yuge Hu, Juntao Feng, Zhiqing Ma*, Xili Liu*, Roman Szostak and Michal Szostak*

*Northwest A&F University, Yangling, Shaanxi 712100, China; Rutgers University, Newark, New Jersey 07102, USA, Email: peng.leinwafu.edu.cn, mazhiqing2000126.com, seedlingnwafu.edu.cn, michal.szostakrutgers.edu

P. Lei, Y. Wang, C. Zhang, X. Hu, J. Feng, Z. Ma, X. Liu, R. Szostak, M. Szostak, Org. Lett., 2022, 24, 6310-6315.

DOI: 10.1021/acs.orglett.2c02534

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Abstract

Air- and moisture-stable [Pd(IPr)(3-CF₃-An)Cl₂] (An = aniline) catalyzes a Sonogashira cross-coupling of aryl ammonium salts. This reaction offers broad scope and excellent C-N activation selectivity in the challenging alkynylative cross-coupling of aryl ammonium salts.

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Key Words

Sonogashira coupling, alkynylation

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ID: J54-Y2022