Synlett
DOI: 10.1055/s-0036-1589098
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Arylation of Benzylic C–H Bonds of Azaarylmethanes with Aryl Sulfides

Ke Gao, Keita Yamamoto, Keisuke Nogi, Hideki Yorimitsu*
  • Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
This work was supported by JSPS KAKENHI Grant Numbers JP16H01019, JP16H04109, JP16H06887, as well as JST ACT-C Grant Number JPMJCR12ZE, Japan. H.Y. thanks the Japan Association for Chemical Innovation, the Tokuyama Science Foundation, and The Naito Foundation for financial support. G.K. acknowledges a JSPS Postdoctoral Fellowship for Foreign Researchers.
Further Information

Publication History

Received: 26 June 2017

Accepted after revision: 17 July 2017

Publication Date:
17 August 2017 (eFirst)

Dedicated to Professor Victor Snieckus in celebration of his 80th birthday

Abstract

Benzylic C–H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.

Supporting Information