DOI: 10.1055/s-0036-1588563
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes

Masakazu Nambo*a, Jacky C.-H. Yima, Kevin G. Fowlera, Cathleen M. Crudden*a, b
  • aInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8602, Japan   Email:
  • bQueen’s University, Department of Chemistry, Chernoff Hall, Kingston, Ontario, K7L 3N6, Canada   Email:
This work was supported by KAKENHI from JSPS (26810056 and 17K17805 to M.N.). M.N. thanks the Chugai Pharmaceutical Company Award in Synthetic Organic Chemistry, Japan. J.C.-H.Y. is a recipient of a JSPS postdoctoral fellowship for research in Japan (16F16749). We also thank JSPS and NU for funding this research through The World Premier International Research Center Initiative (WPI) program
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Publication History

Received: 15 June 2017

Accepted after revision: 19 July 2017

Publication Date:
26 September 2017 (eFirst)

Dedicated to Professor Victor Snieckus, colleague, mentor, and friend on the occasion of his 80th birthday.


The formal cross-dehydrogenative coupling of triarylmethanes with arenes promoted by triflic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is described. This method provides a variety of tetraarylmethane derivatives in good to excellent yields from triarylmethanes that can be readily prepared by our previous methods. Control experiments suggest a possible catalytic cycle involving the generation of a trityl cation intermediate followed by nucleophilic addition of the arene.

Supporting Information