Organic Chemistry Portal



Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts

Sheng-Chun Sha, Sergei Tcyrulnikov, Minyan Li, Bowen Hu, Yue Fu, Marisa C. Kozlowski*, Patrick J. Walsh*

*Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States, Email:,

S.-C. Sha, S. Tcyrulnikov, M. Li, B. Hu, Y. Fu, M. C. Kozlowski, P. J. Walsh, J. Am. Chem. Soc., 2018, 140, 12415-12423.

DOI: 10.1021/jacs.8b05143 (free Supporting Information)

see article for more reactions


KN(SiMe3)2 in combination with a (NIXANTPHOS)Pd catalyst accomplished a deprotonative activation of toluene derivatives to permit cross-coupling with aryl bromides. Good to excellent yields are obtained with a range of electron-rich to neutral aryl bromides. Both electron-rich and electron-poor toluene derivatives are well tolerated.

see article for more examples

Toluene derivative is acidified by cation-π interactions, which is supported computationally and experimentally

Key Words


ID: J48-Y2018