ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Palladium-catalyzed Hiyama cross-couplings of 2-chloro pyrimidines with organosilanes

Hai-Peng Gong, Zheng-Jun Quan, and Xi-Cun Wang

College of Science, Gansu Agricultural University, Lanzhou, People’s Republic of China

E-mail: gonghp@gsau.edu.cn

Received: 19 August 2021  Accepted: 25 December 2021

Abstract:

An efficient synthesis of C2-aryl pyrimidine derivatives via Pd-catalyzed Hiyama couplings has been developed. Various 2-chloro pyrimidines with electron-donating or electron-withdrawing groups as novel electrophile partners coupled well with trimethoxy(phenyl)silane and vinyltrimethoxysilane in the presence of CuCl and TBAF, providing desired products in good to excellent yields. This procedure showed good functional group tolerance, and the electronic and steric effects of 2-chloro pyrimidines seem to be negligible for the transformation.

Keywords: Hiyama coupling; 2-Chloro pyrimidines; Organosilanes; Palladium catalysis; TBAF

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-02044-5

Chemical Papers 76 (4) 2529–2535 (2022)