Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions

Adv Synth Catal. 2017 Jun 6;359(11):1927-1932. doi: 10.1002/adsc.201700380. Epub 2017 May 23.

Abstract

The direct arylation of weakly acidic sp3-hybridized C-H bonds via deprotonated cross-coupling processes (DCCP) is a challenge. Herein, a Pd(NIXANTPHOS)-based catalyst for the mono arylation of 4-pyridylmethyl 2-aryl ethers to generate diarylated 4-pyridyl methyl ethers is introduced. Furthermore, under similar conditions, the diarylation of 4-pyridylmethyl ethers with aryl bromides has been developed. These methods enable the synthesis of new pyridine derivatives, which are common in medicinally active compounds and in application in materials science.

Keywords: 4-pyridylmethyl ethers; aryl bromides; arylation; cross-coupling; diarylartion; palladium-catalyzed.