Synlett
DOI: 10.1055/s-0036-1588563
letter
© 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: mnambo@itbm.nagoya-u.ac.jp
  • bQueen’s University, Department of Chemistry, Chernoff Hall, Kingston, Ontario, K7L 3N6, Canada   Email: cruddenc@chem.queensu.ca
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
Further Information

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.

Abstract

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